Dichloromethane → 2-chloro-6-hydroxy-N,1-dimethyl-1H-indole-3-carboxamide

HRID 1825166Notes

Reaction equation

HRID 1825166 reaction equation
[Cl:1][C:2]1[N:3]([CH3:17])[C:4]2[C:9]([C:10]=1[C:11]([NH:13][CH3:14])=[O:12])=[CH:8][CH:7]=[C:6]([O:15]C)[CH:5]=2.B(Br)(Br)Br.C(Cl)Cl>>[CH3:14][NH:13][C:11]([C:10]1[C:9]2[C:4](=[CH:5][C:6]([OH:15])=[CH:7][CH:8]=2)[N:3]([CH3:17])[C:2]=1[Cl:1])=[O:12]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 221435532-chloro-6-methoxy-N,1-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 221436802-chloro-6-hydroxy-N,1-dimethyl-1H-indole-3-carboxamideYield 85%

Procedure

This material was prepared by reaction of 2-chloro-6-methoxy-N,1-dimethyl-1H-indole-3-carboxamide 75b (0.38 g, 1.4 mmole) with 1.0 M BBr3 in CH2Cl2 (4.19 ml, 4.19 mmole) in a manner as previously described for example 1d to give an off-white solid (0.195 g, 85%). 1NMR (300 MHz, CD3OD) δ 7.61 (1H, d, J=8.3 Hz), 6.65 (1H, s), 6.62 (1H, d, J=2.1 Hz), 3.56 (3H, s) 2.85 (3H, s); ESIMS (MH+): 239.00.

Sources & evidence

ORD record
ord-1cc14342566045c9b6ee614f833e1e1a
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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