Methanol → 3-Benzoyl-10-(3,5-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1071020Notes

Reaction equation

HRID 1071020 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18](Br)=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([F:31])[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(COC)OC.C1COCC1.O>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:27]4[CH:26]=[C:25]([F:24])[CH:30]=[C:29]([F:31])[CH:28]=4)=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 223966193-Benzoyl-10-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Product 1

HCID 223965933-Benzoyl-10-(3,5-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indoleYield 100%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 3-benzoyl -10-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.923 g, 2.5 mmol) and tetrakis(triphenylphosphine)paliadium (0.29 g, 0.25 mmol) in dimethoxyethane (10.0 mL) and a solution of 3,5-difluorophenylboronic acid (0.95 g of a 50% by weight solution in THF/H2O, 3.0 mmol) and sodium carbonate (2 M, 12.0 mL) were reacted in a manner similar to Preparation 1. Column chromatography (silica gel, 1-5% MeOH/CHC1-3) afforded 1.03 g (100%) of a white solid: mp 198-201° C.; 1H NMR (400 MHz, CDCl3) δ 8.32, 7.40-7.28, 7.14, 6.98-6.80, 6.80-6.70, 4.04-3.94, 3.83-3.73, 3.65-3.58, 3.60-3.50, 3.20-3.13, 2.94-2.84, 2.71-2.60, 2.45-2.36; IR (drift) 3235, 3211, 1607, 1466, 1431, 1336, 1291, 1117, 984, 864, 789, 751, 737, 704, 698 cm−1; MS (EI) m/z 402 (M+); Anal. Calcd for C25H20F2N2O: C, 74.61; H, 5.01; N, 6.96. Found: C, 74.57; H, 5.05; N, 6.99.

Sources & evidence

ORD record
ord-5de322b96c5e4341ae0b32f33ac65e1a
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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