Dichloromethane → HCID 22143515, compound

HRID 1825130Notes

Reaction equation

HRID 1825130 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=3)[N:10]([CH3:19])[C:9]=2[CH3:20])=[O:7])[CH2:3][CH2:2]1.B(Br)(Br)Br.C(Cl)Cl>>[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[N:10]([CH3:19])[C:9]=2[CH3:20])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 22143562N-(Cyclopropylmethyl)-6-methoxy-1,2-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 22143515HCID 22143515, compoundYield 77%

Procedure

This material was prepared by reaction of N-(cyclopropylmethyl)-6-methoxy-1,2-dimethyl-1H-indole-3-carboxamide 55a (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 a pale yellow solid (0.278 g, 77%). 1H NMR (400 MHz, CD3OD) δ 7.55 (1H, d, J=8.5 Hz), 6.77 (1H, s), 6.71 (1H, d, J=8.5 Hz), 3.63 (3H, s), 3.28 (2H, m), 2.61 (3H, s), 1.18 (1H, m), 0.56 (2H, m); ESIMS (MH+): 259.10.

Sources & evidence

ORD record
ord-5f5a0c652b9f4f3db8c55efeb20e0234
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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