Dichloromethane → HCID 22143515, compound

HRID 985251Notes

Reaction equation

HRID 985251 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.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

3

Reactant 2

HCID 6344DichloromethaneHCID 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 BBr3in 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) δ7.55 (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-a275dd80596c4aeb8592a03752ea975f
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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