Dichloromethane → 6-hydroxy-1,2-dimethyl-N-(3-morpholin-4-ylpropyl)-1H-indole-3-carboxamide

HRID 985267Notes

Reaction equation

HRID 985267 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:15])=[C:8]([CH3:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.B(Br)(Br)Br.C(Cl)Cl>>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[O:15])=[C:8]([CH3:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 221435776-Methoxy-1,2-dimethyl-N-(3-morpholin-4-ylpropyl)-1H-indole-3-carboxamide

Product 1

HCID 221436336-hydroxy-1,2-dimethyl-N-(3-morpholin-4-ylpropyl)-1H-indole-3-carboxamideYield 104.1%

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-N-(3-morpholin-4-ylpropyl)-1H-indole-3-carboxamide 68a (0.445 g, 1.29 mmole) by treatment with 1.0 M BBr3 in CH2Cl2 (3.86 ml, 3.86 mmole) in a manner as described previously for example 1d to give a white solid (0.445 g, 59%). 1H NMR (300 MHz, CD3OD) δ7.49 (1H, d, J=8.6 Hz), 6.71 (1H, s), 6.64 (1H, dd, J=2.2, 8.6 Hz), 3.87 (4H, m), 3.56 (3H, s), 3.47 (2H, t, J=6.4 Hz), 3.10-3.24 (6H, m), 2.55 (3H, s), 2.00 (2H, m); ESIMS (MH+): 332.15.

Sources & evidence

ORD record
ord-d7a0ff088ecd4eb5a256884305596ab3
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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