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[ CAS No. 99277-71-1 ] {[proInfo.proName]}

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Chemical Structure| 99277-71-1
Chemical Structure| 99277-71-1
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Product Details of [ 99277-71-1 ]

CAS No. :99277-71-1 MDL No. :MFCD01013599
Formula : C7H4BrNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZIRHHEZLJGORGU-UHFFFAOYSA-N
M.W : 246.02 Pubchem ID :3774467
Synonyms :
2-Nitro-4-bromobenzoic acid

Calculated chemistry of [ 99277-71-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.92
TPSA : 83.12 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.294 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0747 mg/ml ; 0.000304 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.01
Solubility : 2.4 mg/ml ; 0.00977 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 99277-71-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99277-71-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 99277-71-1 ]

[ 99277-71-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 99277-71-1 ]
  • [ 74-88-4 ]
  • [ 158580-57-5 ]
YieldReaction ConditionsOperation in experiment
97% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; Compound 7 A (10.0 g, 40.7 mmol) was dissolved in DMF (100 mL). Cs2CO3 (27.0g, 81.3 mmol) and methyl iodide (7.60 mL, 122.0 mmol) were added. The solution was stirred at room temperature overnight. EtOAc (250 mL) and water (100 mL) were added. The organic phase was separated and washed with water (100 mL) three times and brine (50 mL), then dried over Na2SO4) filtered, and concentrated using a rotary evaporator. The product was dried under vacuum to give compound 7B (10.3 g, 97%).
94% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h; Example I-XVIIPreparation of Compound 321General Procedure I-ESTo a mixture of 4-bromo-2-nitrobenzoic acid (10 g, 41 mmol) and K2CO3 (11.3 g, 82 mmol) in 100 mL of DMF was added CH3I (7.1 g, 50 mmol) dropwise and the mixture was stirred at 80 C. for 3 hrs. After cooling to r.t, the mixture was filtered, the filtrated was concentrated under reduced pressure to remove DMF, and the residue was dissolved with EtOAc (50 mL), washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography to give methyl 4-bromo-2-nitrobenzoate (I-XVIIa, 10 g, yield 94%). 1H NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 3.92 (s, 3H).
94% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h; To a mixture of 4-bromo-2-nitrobenzoic acid (10 g, 41 mmol, 1 eq) and K2CO3 (11.3 g, 82 mmol, 2 eq) in 100 mL of DMF was added CH3I (7.1 g, 50 mmol, 1.2 eq) dropwise and the mixture was stirred at 80 C for 3 hrs. After cooling to rt, the mixture was filtered, the filtrated was poured into water and extracted with EtOAc (150 mL x 3), washed with water (150 mL x 3) and brine (150 mL x 2), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography to give methyl 4-bromo-2-nitrobenzoate (10 g, 94%). 1HNMR (300 MHz, DMSO-d6): G 8.34 (s, 1H), 8.08- 8.05 (m, 1 H), 7.85- 7.82 (m, 1 H), 3.85 (s, 3 H).
94.2% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; To a solution of compound 267a (5 g, 4.07 mmol), 4-bromo-2-nitrobenzoic acid in N, N-dimethylformamide (50 mL), cesium carbonate (13.5 g, 40.5 mmol) and methyl iodide (3.8 mL, 61 mmol).The mixture was stirred at room temperature for 16 hours, then the mixture was concentrated under reduced pressure to remove some solvents, water was added to the residue and extracted with ethyl acetate (160 mL × 2), and washed with saturated brine (60 mL × 3),After drying over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (petroleum ether: ethyl acetate = 91: 9) to obtain a white solid compound 267b, namely 4-bromo-2-nitrobenzene Methyl formate (4.98 g, 94.2% yield.
90% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; A. Methyl 2-amino-4-bromobenzoate To a stirred solution of 4-bromo-2-nitrobenzoic acid (EXAMPLE 5) (3.81 g, 15 mmol) in DMF (30 mL) at 0 C. was added 1,8-diazabicycloundecane (DBU) (10.3 mL, 75 mmol) followed by methyl iodide (4.67 mL, 75 mmol). The reaction mixture was stirred 15 min at 0 C. then allowed to warm to room temperature and stir overnight. The mixture was poured into water and extracted with EtOAc (2*). The combined organic extracts were washed with water (2*), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexanes/EtOAc) to afford methyl 4-bromo-2-nitrobenzoate as a pale yellow solid (3.52 g, 90%).
90% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 - 20℃; B. Methyl 2-amino-4-bromobenzoate. ; To a stirred solution of 4-bromo-2-nitrobenzoic acid (3.81 g, 15 mmol) in DMF (30 mL) at 0 C. was added 1,8-diazabicycloundecane (DBU; 10.3 mL, 75 mmol) followed by Mel (4.67 mL, 75 mmol). The mixture was stirred for 15 min at 0 C., then was allowed to warm to rt and was stirred overnight. The mixture was poured into water and extracted with EtOAc (2×). The combined organic extracts were washed with water (2×), dried (MgSO4), and concentrated. The residue was purified by flash chromatography (hexanes/EtOAc) to afford methyl 4-bromo-2-nitrobenzoate as a pale yellow solid (3.52 g, 90%). To a solution of the nitrobenzoate (3.52 g, 13.5 mmol) in 1:1 EtOAc/DCM (30 mL) at rt was added SnCl2.2H2O (15.27 g, 67 mmol). After 18 h, the mixture was concentrated, diluted with satd. aq. NaHCO3, and extracted with DCM (3×). The combined organic layers were dried (MgSO4) and concentrated to provide the desired aminobenzoate as a white solid (2.89 g, 93%). 1H NMR (400 MHz, CDCl3): 7.70(d, J=8.6, 1H), 6.84 (d, J=1.9, 1H), 6.75 (dd, J=8.6, 1.9, 1H), 5.78 (br s, 2H), 3.86 (s, 3H).
90 - 98% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 - 20℃; for 48.25 - 72.25h;Product distribution / selectivity; Example 62:; N-[7-ethyI-6-(l-methyI-lH-pyrazol-4-yl)-2,4-dioxo-l,4-dihydro-2H-quinazoIin-3-yI]- methanesulfonamide; 4-Bromo-2-nitro-benzoic acid methyl ester; To a solution of 4-bromo-2-nitrobenzoic acid (25.3 g, 103 mmol) in DMF (200 mL) at 0 0C were added DBU (79.1 mL, 514.8 mmol) and MeI (32.2 mL, 515 mmol). The reaction mixture was stirred for 15 min at this temperature and for 72 h at r.t. The mixture was poured into water and extracted with EtOAc (2X). The combined organic layers were washed with water (2X), dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by flash chromatography (silica gel, 7:3 hexanes:EtOAc) to provide the title compound (26.24 g, 98%) as a yellow oil.; Example 71:; N-[7-(l,l-difluoro-ethyl)-6-(2-isopropyl-2H-pyrazol-3-yl)-2,4-dioxo-l,4-dihydro-2H- quinazolin-3-yl]-methanesulfbnamide; 4-Bromo-2-nitro-benzoic acid methyl ester; To solution of 4-bromo-2-nitro-benzoic acid (9 g, 36.58 mmol) in dimethylforrnamide (36 mL) cooled to 0 0C were added l,8-diazabicyclo[5.4.0]und-7-ene (28.09 mL, 182.9 mmol) and MeI (11.4 mL, 182.5 mmol). The reaction mixture was stirred at 0 0C for 15 min and at r.t. for 48 h. The mixture was poured into water and extracted with EtOAc (2X). The combined organic phases were washed with water (2X), dried (Na2SO4) and concentrated to dryness. The crude product was purified by flash chromatography (hexanes to EtOAc / hexanes (4:6)) to give 4-bromo-2-nitro-benzoic acid methyl ester (8.62 g, 33.147 mmol, 90%). 1H-NMR (CDCl3, 400 MHz) 8.02 (s, 1 H), 7.81 (dd, J= 2.3, 10.5Hz IH), 7.66 (d, J= 8.2 Hz, IH), 3.92 (s, 3H).
78% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h; To a solution of 4-bromo-2-nitrobenzoic acid (10 g, 40.6 mmol) in DMF (100 mL) was added potassium carbonate (11.24 g, 81 mmol) followed by methyl iodide (3.30 mL, 52.8 mmol) dropwise. The mixture was stirred at 80 C. for 3 h. After cooling to room temperature, the mixture was filtered and residue was dissolved in ethyl acetate (2*200 mL). The organic layer was washed with water (200 mL) followed by brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude sample was purified by flash chromatography (5% Ethyl acetate: Pet ether; 80 g silica gel column) to afford 1A (off white solid, 8.2 g, 31.5 mmol, 78% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.35 (d, J=2.0 Hz, 1H), 8.07 (dd, J=8.0, 1.6 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 3.85 (s, 3H).
0.90% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; To a stirred solution of 4-bromo-2-nitrobenzoic acid (3.8 g, 15 mmol) in DMF (30 mL) at 0 C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10.0 mL, 75.0 mmol) followed by iodomethane (4.7 mL, 75 mmol). The reaction mixture was stirred 15 min at 0 C., then was allowed to warm to room temperature and was stirred overnight. The mixture was poured into H2O and extracted with EtOAc (2×). The combined organic extracts were washed with H2O (2×), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexanes/EtOAc) to afford methyl 4-bromo-2-nitrobenzoate as a pale yellow solid (3.52 g, 0.90%). To a solution of the nitrobenzoate (3.52 g, 13.5 mmol) in 1:1 EtOAc/DCM (30 mL) at room temperature was added SnCl2.2H2O (15 g, 67 mmol). The reaction mixture was allowed to stir overnight. The solvents were evaporated in vacuo, and the residue was partitioned between satd. aq. NaHCO3 and DCM. The layers were separated, and the aqueous layer was further extracted with DCM (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to provide the pure aminobenzoate as a white solid (2.89 g, 93%). 1H NMR (400 MHz, CDCl3): 7.70 (d, J=8.6 Hz, 1H), 6.84 (d, J=1.9 Hz, 1H), 6.75 (dd, J=8.6, 1.9 Hz, 1H), 5.78 (br s, 2H), 3.86 (s, 3H).

  • 2
  • [ 67-56-1 ]
  • [ 99277-71-1 ]
  • [ 158580-57-5 ]
YieldReaction ConditionsOperation in experiment
78% With sulfuric acid; In water; for 16h;Heating / reflux; Step 1. Preparation of Methyl 4-bromo-2-nitrobenzoate Add concentrated sulfuric acid (7 mL) to a solution of commercially available 4- bromo-2-nitrobenzoic acid (25.0 g, 102 mmol) in methanol (150 mL), and heat at reflux for 16 hours. Cool the reaction to room temperature and pour into water (500 mL) and adjust the pH of the suspension to 9 with solid sodium carbonate. Extract the solution with ethyl acetate (2 x 250 mL), then combine the organic extracts and wash with brine (100 mL), dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a pale amber oil, which crystallizes upon standing (20.5 g, 78%)
With sulfuric acid; for 4h;Reflux; (Example 22-1) To a methanol solution (50 ml) of 4-bromo-2-nitrobenzoic acid (2.54 g) was added concentrated sulfuric acid (1.0 ml), followed by heating at reflux for 4 hours. The reaction solution was concentrated under reduced pressure, and water (20 ml) was added to the residue. Under ice cooling, 5 N aqueous sodium hydroxide solution (2.0 ml) and a saturated aqueous sodium hydrogen carbonate solution were added, and extracted with dichloromethane. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford methyl 4-bromo-2-nitrobenzoate (619 mg). 1H NMR (500 MHz, CDCl3) delta: 3.95 (s, 3H), 7.69 (d, 1H, J = 8.3 Hz), 7.84 (dd, 1H, J = 8.3, 2.0 Hz), 8.05 (d, 1H, J = 2.0 Hz).
  • 3
  • [ 99277-71-1 ]
  • [ 77-78-1 ]
  • [ 158580-57-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; at 20 - 50℃; for 1h; To acetone 40mL solution of 4-bromo-2-nitrobenzoic acid 4.0g were added potassium carbonate 3.4g and dimethylsulfate 2.3mL at room temperature, and it was stirred at 50C for 1 hour. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. Water and ethyl acetate were added to the obtained residue. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution, 1.0mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure to give methyl 4-bromo-2-nitrobenzoate 4.1g of white solid. 1H-NMR(CDCl3) delta value: 3.97(3H,s),7.85(1H,d,J=8.3Hz),8.07(1H,dd,J=8.3,2.0Hz),8 .47(1H,d,J=2.0Hz).
  • 4
  • [ 507-19-7 ]
  • [ 99277-71-1 ]
  • [ 890315-72-7 ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In methanol; N,N-dimethyl acetamide; water; ethyl acetate; Referential Example 2 To 50 mL of N,N-dimethylacetamide solution containing 5.0 g of 4-bromo-2-nitrobenzoic acid, 41 g of potassium carbonate, 4.6 g of benzyltriethylammonium chloride and 69 mL of 2-bromo-2-methylpropane were added at room temperature and stirred at 55C for 10 hours. After the reaction mixture was cooled to room temperature, 12 mL of 2-bromo-2-methylpropane was added and stirred at 55C for 4 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Methanol was added to the obtained residue and solid substances were separated by filtration to obtain 3.0 g of tert-butyl 4-bromo-2-nitrobenzoate as white solid. 1H-NMR (CDCl3) delta: 1.55 (9H, s), 7.63 (1H, d, J = 8.3 Hz), 7.77 (1H, dd, J = 8.3, 1.9 Hz), 7.95 (1H, d, J = 1.9 Hz).
With potassium carbonate;N-benzyl-N,N,N-triethylammonium chloride; In ISOPROPYLAMIDE; at 20 - 55℃; for 14.0h; To N,N-dimethylacetamide 50mL solution of 4-bromo-2-nitrobenzoic acid 5.0g were added potassium carbonate 41g, benzyltriethylammonium chloride 4.6g and 2-bromo-2-methylpropane 69mL at room temperature and it was stirred at 55C for 10 hours. After the reaction mixture was cooled to room temperature, 2-bromo-2-methylpropane 12mL was added to it, and it was stirred at 55C for 4 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Methanol was added to the obtained residue, solid matter was filtrated to give tert-butyl 4-bromo-2-nitrobenzoate 3.0g of white solid. 1H-NMR(CDCl3) delta value: 1.55(9H,s),7.63(1H,d,J=8.3Hz),7.77(1H,dd,J=8.3,1.9Hz),7 .95(1H,d,J=1.9Hz).
  • 5
  • [ 99277-71-1 ]
  • [ 158580-57-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; dimethyl sulfate; In water; ethyl acetate; acetone; Referential Example 1 To 40 mL of acetone solution containing 4.0 g of 4-bromo-2-nitrobenzoic acid, 3.4 g of potassium carbonate and 2.3 mL of dimethyl sulfate were added at room temperature and stirred at 50C for 1 hour. After the reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the obtained residue. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution, 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure to obtain 4.1 g of methyl 4-bromo-2-nitrobenzoate as white solid. 1H-NMR (CDCl3) delta: 3.97 (3H, s), 7.85 (1H, d, J = 8.3 Hz), 8.07 (1H, dd, J = 8.3, 2.0 Hz), 8.47 (1H, d, J = 2.0 Hz).
  • 6
  • [ 99277-71-1 ]
  • [ 1211596-82-5 ]
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; ;