(3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-carbamic acid tert-butyl ester → (3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-amine
Reaction equation
C(OC(=O)[N:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH3:17])(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[F:25])[CH2:18][NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH3:17]Participants
4
Procedure
A solution of compound 125-C (2.7 g, 6.9 mmol) in dichloromethane (40 mL) and trifluoroacetic acid (40 mL) was stirred at rt for 4 h. The solvent was evaporated in vacuo, and the residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, and the solvent evaporated in vacuo to afford compound 125-D as a colorless solid (1.86 g, 93%). 1H-NMR (CDCl3): δ 2.16 (s, 3H), 4.37 (s, 2H), 7.09-7.32 (m, 5H), 7.40 (d, 1H), 7.60 (d, 1H); MS: m/z 290.1 (MH+).