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[ CAS No. 6326-79-0 ] {[proInfo.proName]}

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Chemical Structure| 6326-79-0
Chemical Structure| 6326-79-0
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Product Details of [ 6326-79-0 ]

CAS No. :6326-79-0 MDL No. :MFCD01631138
Formula : C8H4BrNO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :HVPQMLZLINVIHW-UHFFFAOYSA-N
M.W : 226.03 Pubchem ID :95716
Synonyms :

Calculated chemistry of [ 6326-79-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.86
TPSA : 46.17 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.01
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.32

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.803 mg/ml ; 0.00355 mol/l
Class : Soluble
Log S (Ali) : -1.9
Solubility : 2.84 mg/ml ; 0.0126 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.64
Solubility : 0.0521 mg/ml ; 0.000231 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 6326-79-0 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338-P310 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6326-79-0 ]

* 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 [ 6326-79-0 ]

[ 6326-79-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 6326-79-0 ]
  • [ 77-78-1 ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
85% With sodium carbonate; In acetone; at 60℃; for 20h; To a solution of 3a (150 mg, 0.66 mmol) in dry acetone (30 mL) was added Na2CO3 (anh. ) (1.0 g) and dimethylsulfate (0.8 mL) under Ar and the reaction mixture was heated at 60 C for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C). The solid residue was submitted to flash chromatography with CH2C12 to afford lla (140 mg, 0.58 mmol, 85%) (see Scheme 2 in Fig. 2B).
63% The 1.15g (5mmol) 6- bromo-isatin was dissolved in 10mL DMF,1.03 g (7.5 mmol) of potassium carbonate was added with stirring.Then, 0.804 g (6.25 mmol) of dimethyl sulfate was added dropwise, and the mixture was reacted at room temperature for 4 hours, and the mixture was poured into 100 mL of ice water.The extract was extracted with ethyl acetate (60 mL×3), and the organic layer was evaporated.After concentrated to dryness, it was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 20:3)0.753 g of a red solid was obtained in a yield of 63%.
With sodium hydride; In N,N-dimethyl-formamide;Inert atmosphere; General procedure: A mixture of 2-bromoaniline or 3-bromoaniline (110 mmol, 18.9 g), chloral hydrate (118.8 mmol,19.6 g), anhydrous sodium sulfate (880 mmol, 125 g), and hydroxylamine hydrochloride (347.6mmol, 24.2 g) in water (700 mL) was heated under reflux for 25 min to form a yellow precipitate. 50mL of ethanol was added after that and left to boil for another 4 min before filtration. The resultedisonitrosoacetanilide was then heated with sulfuric acid (150 mL) at 70 C for about 10 min thenpoured into ice water to form an orange precipitate. When using 3-bromoaniline, an extra step ofseparation is required by solving the resulted mixture in 0.25 M NaOH (1 L), filtering it, then addingacetic acid (100 mL) to afford 4-bromoistain as a precipitate. 6-Bromoistin can be then obtained whenlowering the pH of the solution to 1 by hydrochloric acid 37%.All substituted bromo-isatins were methylated by stirring (22 mmol, 4.97 g) with sodiumhydride (2 mmol, 0.968 g) and dimethylsulfate (23.1 mmol, 2.19 mL) in dried DMF (50 mL) undernitrogen atmosphere. The resulting mixture was poured after 2 h in ice water (100 mL) to form anorange precipitate.The methylated bromo-isatins (2 mmol, 0.480 g) were treated after that with oxindole (2 mmol,0.226 g) in a 100:1 mixture of glacial acetic acid and hydrochloric acid 37% (12 mL) in reflux for about 3 h. Then, they were poured in ice water (50 mL) to afford 5-, 6- and 7-bromomeisoindigo. While 4'-, 5'-, 6'- and 7'-bromomeisoindigo were obtained by reacting unmethylated bromo-isatins(2 mmol, 0.452 g) with 1-methyloxindole (2 mmol, 0.294 g) in the same conditions. The resultedprecipitates were washed with water, ethanol (2 x 10 mL), and diethylether (2 10 mL) then dried.
  • 2
  • [ 6326-79-0 ]
  • [ 74-88-4 ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; In acetonitrile; at 60℃; for 1.5h; To a solution of 6-bromoindoline-2,3-dione (0.504 g,2.23 mmol)in acetonitrile (11 mL)was added K2C03 (1.23 g,8.92 mmol)then iodomethane (0.278 mL,4.46 mmol). The reactionmixture was heated at 60 oc for 1.5 h. After cooling to room temperature,water (30 mL)wasadded and the mixture was extracted with DCM (30 mL x 3). The combined organic layers were washed with brine (30 mL),dried over anhydrous Na2S04 and then concentrated in underreduced pressure to give the title compound (0.506 g,95%)that required no further purification.1HNMR(400MHz,CDCl3)87.46(dd,J=7.9,l.OHz,1H),7.32-7.28(m,1H),7.08(d,J=1.5 Hz,1H),3.25 (d,J = 0.6 Hz,3H).
65% With potassium carbonate; In acetonitrile; at 60℃; for 0.75h; To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Mel (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C for 45 min DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; Step 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R7 (25.0 g, I I I mmol) in acetonitrile (750 mL) is added Mel (15 mL, 24ltnmol) and KzC03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, dried over MgS04 and concentrated. Yield 56%, mlz 240/242 [M+H]+,rt 0.48 min, LC-MS Method XOOl_ 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; Step 1: Synthesis of Intermediate 1-5.1To RiO (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 mL, 241 mmol) and K2C03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, is dried over MgSO4 and concentrated. Yield 56%, m/z 240/242[M+H]+, rt 0.48 mi LC-MS Method X001 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; Synthesis of 1-Methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one (R7) Step 1: Synthesis of Intermediate I-4.1 [0293] To R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
With potassium carbonate; In acetonitrile; at 60℃; for 0.666667h; To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*
General procedure: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 C (ice bath), whereupon sodium hydride (60% dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 C for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90%-100% yield).
With sodium hydride; In N,N-dimethyl-formamide; at 0℃; General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

  • 3
  • [ 6326-79-0 ]
  • MeX, X = halide [ No CAS ]
  • [ 667463-64-1 ]
  • 4
  • [ 6326-79-0 ]
  • [ 34557-54-5 ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In acetonitrile; at 60℃; for 0.75h; To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Met (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C. for 45 min. DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.
  • 5
  • [ 6326-79-0 ]
  • methylating agent [ No CAS ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R10 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Met (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, is dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
  • 6
  • [ 6326-79-0 ]
  • CH3-X, X=halide [ No CAS ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; General procedure: To a solution of 6-bromoindoline-2,3-dione (7a) or 6-bromo-7-methylindoline-2,3-dione (7b) (3.94mmol) in dry N, N-dimethylformamide (5mL) was added K2CO3 (1.3g, 9.44mmol) and alkyl halides (4.72mmol) at 0C. The reaction mixture was stirred at 65C for 1-2h. After completion of reaction as determined by TLC analysis, the reaction solution was poured into water (25mL) and extracted with CH2Cl2 (3×100mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate 10:1-3:1) to afford 8a-8c. 6-Bromo-1-methylindoline-2, 3-dione (8a) Yield 90%; 1H NMR (400 MHz, CDCl3) delta 3.26 (s, 3H), 7.09 (s, 1H), 7.29-7.31 (m, 1H), 7.47 (d, 1H, J = 8.0 Hz). 13C NMR (100 MHz, CDCl3) delta 26.4, 113.7, 116.1, 126.3, 127.1, 133.7, 152.2, 158.1, 182.1.
  • 7
  • [ 6326-79-0 ]
  • [ 1131-18-6 ]
  • [ 50607-30-2 ]
  • 6-bromo-3'-methyl-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b][1,6]naphthyridine]-2,5'(1'H)-dione [ No CAS ]
  • 8
  • [ 6326-79-0 ]
  • [ 112253-70-0 ]
YieldReaction ConditionsOperation in experiment
81% With ammonium hydroxide; dihydrogen peroxide; In dimethyl sulfoxide; at 20 - 30℃; for 4h;Sealed tube; General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).
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; ;