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[ CAS No. 676448-17-2 ] {[proInfo.proName]}

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Chemical Structure| 676448-17-2
Chemical Structure| 676448-17-2
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Product Details of [ 676448-17-2 ]

CAS No. :676448-17-2 MDL No. :MFCD04117874
Formula : C13H14BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZGBNKNOAADXGOH-UHFFFAOYSA-N
M.W : 296.16 Pubchem ID :40425427
Synonyms :

Calculated chemistry of [ 676448-17-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.31
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.84
TPSA : 31.23 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.26
Log Po/w (XLOGP3) : 3.96
Log Po/w (WLOGP) : 4.19
Log Po/w (MLOGP) : 3.29
Log Po/w (SILICOS-IT) : 2.74
Consensus Log Po/w : 3.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.36
Solubility : 0.0128 mg/ml ; 0.0000432 mol/l
Class : Moderately soluble
Log S (Ali) : -4.32
Solubility : 0.0143 mg/ml ; 0.0000483 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.2
Solubility : 0.0187 mg/ml ; 0.0000631 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 676448-17-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 676448-17-2 ]

* 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 [ 676448-17-2 ]

[ 676448-17-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 52488-36-5 ]
  • [ 34619-03-9 ]
  • [ 676448-17-2 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydride; In tetrahydrofuran; mineral oil; for 22h; Add DI-TERT-BUTYL dicarbonate (1.4 g. 6.4 mmol) and sodium hydride (0.15 g, 60% dispersion in mineral oil, 3.8 mmol) to a solution of 4-bromoindole (0.4 mL, 3.2 mmol) in THF (11 mL) at 0 C. Stir the reaction for 22 h, quench with saturated aqueous ammonium chloride, and extract with methylene chloride. Dry the combined organic extracts with sodium sulfate, filter, and concentrate in vacuo. Purify by flash column chromatography, utilizing the appropriate mixture of hexanes and methylene chloride, to provide 0.85 g (90%) of the titled compound as a clear, colorless OIL.'H NMR (CDC13) 8 8. 10 (d, J = 8 HZ, 1H), 7.63 (d, J = 4 Hz, 1H), 7. 38 (d, J = 8 HZ, 1H), 7.16 (t, J = 8 Hz, 1H), 6.64 (d, J = 4 Hz, 1H), 1.67 (s, 9H). TLC (SI02) : Rf 0. 3 (9: 1 hexanes/methylene chloride).
  • 2
  • [ 52488-36-5 ]
  • [ 24424-99-5 ]
  • [ 676448-17-2 ]
YieldReaction ConditionsOperation in experiment
100% With dmap; In tetrahydrofuran; for 0.25h; Di-tert-butyl dicarbonate (17 g, 76.5 mmol) was added to a solution of 4-Bromoindole 4-1 (10 g, 51 mmol) and DMAP (0.62 g, 0.51 mmol) in THF (120 mL). The reaction mixture was stirred for 15 minutes, and then stripped. The remaining oil was partitioned between ether and water. The ether layer was washed with 3*50 mL of saturated sodium bicarbonate and 1*75 mL of brine. The ether layer was dried over magnesium sulfate, filtered and stripped. The remaining brown oil was chromatographed over silica gel eluding with 1:100 ethyl acetate: hexanes to afford 15 g (100% yield) of 4-bromo-indole-1-carboxylic acid-tert-butyl ester 4-2.
99% In dichloromethane; at 20℃; for 8h; To a solution of 4-bromoindole (1.96 g, 10 mmol) in dichloromethane (50 mL),DMAP (122 mg, 1 mmol) and di-tert-butyl dicarbonate (2.4 g, 11 mmol) were added,The reaction system is stirred at room temperature for 8 hours.Work-up gave tert-butyl 4-bromo-1H-indol-1-yl carbonate (2.96 g, 99% yield).
95% With dmap; In dichloromethane; at 20℃; for 0.25h;Inert atmosphere; Sealed tube; Boc2O (3.5 mL, 15.3 mmol) was added to a stirred solution of 4-bromo-1H-indole (2 g, 10.2 mmol) and 4-DMAP (62 mg, 0.5 mmol) in dichloromethane (30 mL). The reaction mixture was stirred at ambient temperature for 15 min. Water (40 mL) was added and the layers were separated. Aqueous phase was extracted with additional dichloromethane (30 mL). The combined organic extracts were washed with water, aqueous sodium chloride solution, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (0-2% ethyl acetate in pet-ether) to afford compound 4 (2.86 g, 95% yield) as a colour less liquid. 1H NMR (CDCl3, 400 MHz): delta 1.67 (S, 9H), 6.63 (d, 1H, J=3.6 Hz), 7.16 (t, 1H, J=8 Hz), 7.38 (d, 1H, J=8 Hz), 7.64 (d, 1H, J=3.6 Hz), 8.11 (d, 1H, J=8.4 Hz). 13C NMR (CDCl3, 100 MHz): delta 28.13, 84.23, 107.06, 114.22, 114.66, 125.11, 125.52, 126.44, 131.12, 135.55, 149.43
85% With dmap; triethylamine; In acetonitrile; at 20℃; for 2h; Step 84a: 7?rt-butyl 4-bromo-lH-indole-l-carboxylate (Compound 0601-176)The solution of 4-bromoindole (394 mg, 2.00 mmol), (Boc)20 (523 mg, 2.40 mmol), DMAP (293 mg, 2.4 mmol) and Et3N (0.4 mL) in MeCN (6 mL) was stirred at room temperature for 2 hours. The solvent was removed and the residue was dissolved in ethyl acetate (40 mL), washed with water (3 x 20 mL) and brine (1 x 20 mL), the organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to afford compound 0601-176 (508 mg, 85%) as a colorless oil. 1H-NMR (400 MHz.OMSO-d6) delta 1.64 (s, 9H), 6.67 (d, J= 3.2 Hz, 1H), 7.28 (t, J= 8.0 Hz, 1H), 7.48 (m, 1H),7.80 (d, J= 3.2 Hz, 1H), 8.08 (m, 1H).
85% With dmap; triethylamine; In acetonitrile; at 20℃; for 2h; Step 84a: Tert-butyl 4-bromo-1H-indole-1-carboxylate (Compound 0601-176)[0559]The solution of 4-bromoindole (394 mg, 2.00 mmol), (Boc)2O (523 mg, 2.40 mmol), DMAP (293 mg, 2.4 mmol) and Et3N (0.4 mL) in MeCN (6 mL) was stirred at room temperature for 2 hours. The solvent was removed and the residue was dissolved in ethyl acetate (40 mL), washed with water (3×20 mL) and brine (1×20 mL), the organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to afford compound 0601-176 (508 mg, 85%) as a colorless oil. 1H-NMR (400 MHz. DMSO-d6) delta 1.64 (s, 9H), 6.67 (d, J=3.2 Hz, 1H), 7.28 (t, J=8.0 Hz, 1H), 7.48 (m, 1H), 7.80 (d, J=3.2 Hz, 1H), 8.08 (m, 1H).
85% With dmap; triethylamine; In acetonitrile; at 20℃; for 2h; MeCN (6 mL) solution of 4-bromo-indole (394mg, 2.00mmol), (Boc) 2O (523mg, 2.40mmol), was DMAP (293mg, 2.4mmol) to a solution of and Et3N (0.4mL) was stirred at room temperature for 2 hours . The solvent was removed and the residue was dissolved in ethyl acetate (40 mL), washed with water (3 × 20 mL) and brine (1X20mL), and the organic layer concentrated, and purified by column chromatography on silica gel (petroleum ether) on, to give compound 0601-176 as a colorless oil (508mg, 85%).
76% With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h; To a solution of 4-bromo-lH-indole (LXXXVII) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added B0C2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXXVIII) as white solid (11.4 g, 38.5 mmol, 76% yield). NMR (CDC13, 400 MHz) delta ppm 1.68 (s, 9H), 6.64 (d, J=4Hz, 1H), 7.17 (t, J=8.4Hz, 1H), 7.39 (d, J=7.6Hz, 1H), 7.64 (d, J=3.2Hz, 1H), 8.11 (d, J=8.0Hz, 1H); ESIMS found for Ci3Hi4BrN02 mlz 297.1 (M+H).
76% With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h; To a solution of 4-bromo-1H-indole (LXX) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added Boc2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give tert-butyl 4-bromo-1H-indole-1-carboxylate (LXXI) as white solid (11.4 g, 38.5 mmol, 76% yield). 1H NMR (CDCI3, 400 MHz) delta ppm 1.68 (s, 9H), 6.64 (d, J=4Hz, 1H), 7.17 (t, J=8.4Hz, 1H), 7.39 (d, J=7.6Hz, 1H), 7.64 (d, J=3.2Hz, 1H), 8.11 (d, J=8.0Hz, 1H); ESIMS found for C13H14BrNO2 m/z 297.1 (M+H).
76% With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h; To a solution of 4-bromo-1H-indole (LXX) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added Boc2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give tert-butyl 4-bromo- 1H-indole- 1 -carboxylate (LXXI) as white solid (11.4 g, 38.5 mmol, 76% yield). ?HNMR(CDC13, 400 MHz) Eppm 1.68 (s, 9H), 6.64 (d,J=4Hz, 1H), 7.17 (t,J=8.4Hz, 1H), 7.39 (d,J=7.6Hz, 1H), 7.64 (d,J=3.2Hz, 1H), 8.11 (d, J8.OHz, 1H); ESIMS found for C,3H,4BrNO2 mlz 297.1 (M+H).
66.19% To a suspension of 60% NaH (0.449 g, 11.2 mmol) in dry THF (20.0 mL) was added a solution of compound 1 (2.000 g, 10.20 mmol) in THF (20.0 mL) at -78 C. The reaction mixture was stirred for 1 h. A solution of ditertiary butyl dicarbonate (2.58 mL, 11.2 mmol) in THF (20.0 mL) was added to the above solution drop-wise at -78 C. and stirred at rt for 16 h The reaction progress was monitored by diluting an aliquot of the reaction mixture with water and extracting with EtOAc. The organic layer was spotted over an analytical silica gel TLC plate and visualized using 254 nm UV light. The reaction progressed to completion with the formation of a non-polar spot. The Rf values of the starting material and product were 0.3 and 0.5, respectively. The reaction mixture was poured into ice water (75.0 mL) and extracted with EtOAc (2×100.0 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude compound 2. The crude compound was purified by flash column using 230-400 mesh silica gel and eluted with 8% EtOAc in petroleum ether to afford compound 2 as a brown liquid. TLC system: 5% EtOAc in petroleum ether. Yield 2.000 g (66.19%).
With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h; To a solution of 4-bromo-lH-indole (LXX) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added B0C2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 hours. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXI) as white solid (11.4 g, 38.5 mmol, 76% yield). NMR (CDC13, 400 MHz) delta ppm 1.68 (s, 9H), 6.64 (d, J=4Hz, 1H), 7.17 (t, J=8.4Hz, 1H), 7.39 (d, J=7.6Hz, 1H), 7.64 (d, J=3.2Hz, 1H), 8.11 (d, J=8.0Hz, 1H); ESIMS found for Ci3Hi4BrN02 mlz 297.1 (M+H).
With dmap; In tetrahydrofuran; for 0.5h; Di-tert-butyl dicarbonate (5.33 mL, 22.95 mmol) was added to a solution of 4-bromo-1H-indole (3.00 g, 15.30 mmol) and DMAP (4-dimethylaminopyridine) (0.187 g, 1.530 mmol)) in tetrahydrofuran (20 mL). The reaction mixture was stirred for 30 minutes. The mixture was partitioned between ether (100 mL) and water (100 mL). The ether layer was washed with (3*50 mL) of saturated aqueous sodium bicarbonate and 75 mL of brine. The ether layer was dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed over silica gel eluting with 1:100 ethyl acetate: petroleum ether to afford the title compound.

  • 3
  • [ 52488-36-5 ]
  • [ 6627-89-0 ]
  • [ 676448-17-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; for 18h; A solution of 0.48 mL (3.8 mmol) of 4-bromo-lH-indole in 1 mL of THF was added to a suspension of 0.15 g (6.3 mmol) of NaH in 5 mL of THF, followed by 1.2 mL (6.3 mmol) of tert-butyl phenylcarbonate. The reaction solution was stirred 18 h, then quenched with1 mL of iPrOH, poured into 100 mL of Et2O and washed twice with a saturated aqueous solution of NH4Cl and thrice with water. The organic solvent was removed in vacuo and the residue was purified by flash chromatography eluting with neat hexane to yield the title compound. MS (M-BOC+2H)+ 196.
  • 4
  • [ 676448-17-2 ]
  • [ 79099-07-3 ]
  • [ 676448-18-3 ]
YieldReaction ConditionsOperation in experiment
19% A solution of <strong>[676448-17-2]4-bromo-indole-1-carboxylic acid-tert-butyl ester</strong> 4-2 (4.9 g, 16.5 mmol) in THF (150 mL) under Argon was cooled to -70 C., and n-BuLi (12.4 mL, 24.8 mmol) was added over 20 min. The reaction mixture was warmed to -5 C. in an ice bath and was stirred at this temperature for 30 min. The mixture was cooled to -70 C. and a solution of N-Boc-piperidone 4-3 (3.3 g, 16.5 mmol) in THF (10 mL) was added over 15 min. The reaction was stirred for 45 min at -70 C. and was then warmed to room temperature. The reaction was quenched with a saturated solution of ammonium chloride (75 mL) and partitioned between water (25 mL) and ethyl acetate (75 mL). The organic layer was washed with water (50 mL) and brine (50 mL), then dried (MgSO4), filtered and concentrated. The remaining brown oil was chromatographed, eluding with ethyl acetate:hexanes (1:9) to afford 1.32 g (19% yield) of 4-(1-tert-butoxycarbonyl-4-hydroxy-piperidin-4-yl)-indole-1-carboxylic acid tert-butyl ester 4-4.
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