HCID 22339810, compound → HCID 22339837, compound

HRID 916170Notes

Reaction equation

HRID 916170 reaction equation
[C:1]([NH:4][C:5]1[C:6]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:7]=2S[C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]>[Ni]>[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH:5]([C:6]1[CH:7]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 22339810HCID 22339810, compound

Product 1

HCID 22339837HCID 22339837, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Methyl 3-acetamido-6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (0.7014 g, 2.21 mmol) was reductively desulfurized using Raney nickel to yield the title compound as a clear oil (0.5961 g, 2.05 mmol, 92.6%); TLC: Rf=0.52 (Solvent I), 0.86 (Solvent L); IR (cm−1): 3340 (NH), 1736 (ester C═O), 1654 (amide C═O); 1H nmr (DMSO-d6): δ 8.45 (d, 1H, J=8.0 Hz), 7.59 (d, 2H, J=8.3 Hz), 7.49 (d, 2H, J=8. J z), 5.25 (q, 1H, J=7.6, 15 Hz), 3.55 (s, 3H), 2.75 (m, 2H), 1.82 (s, 3H).

Sources & evidence

ORD record
ord-05286fc0b32244a9808abae6385b8c97
Source dataset
uspto-grants-2007_09
Patent number
US07268164B2

Reaction notes

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