Acetic Acid → 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-7-(trifluoromethyl)-9H-pyrido[2,3-b]indole acetate
Reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([CH3:22])=[C:14]([NH2:23])[C:13]=2[C:24]2[C:25](F)=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH3:32][C:33]([OH:35])=[O:34]>>[C:33]([OH:35])(=[O:34])[CH3:32].[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([CH3:22])=[C:14]3[C:13]=2[C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[N:26][C:25]=2[NH:23]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]Participants
Procedure
3′-(ethylsulfonyl)-2-(2-fluoro-5-methylpyridin-3-yl)-4-methyl-5-(trifluoromethyl)biphenyl-3-amine (4.9 g, 10.8 mmol) was dissolved in HOAc (35 mL) and heated at reflux for 3 h. The reaction mixture was cooled to room temperature affording a crystalline product. The resulting suspension was filtered, rinsed with HOAc (3×5 mL) followed by H2O (3×10 mL) and the solids dried in vacuo to give 3.73 g (70%) of the title compound as a white solid. NMR analysis confirmed that the product was isolated as the mono-acetate salt. 1H NMR (400 MHz, DMSO-d6): δ 12.35 (s, 1H), 12.0 (s, 1H), 8.39 (s, 1H), 8.15 (s, 1H), 8.04-8.09 (m, 2H), 7.90 (t, 1H), 7.51 (s, 1H), 7.42 (s, 1H), 3.43 (q, 2H), 2.76 (s, 3H), 2.28 (s, 3H), 1.91 (s, 3H), 1.18 (t, 3H). MS (ES) [m+H] calc'd for C22H19F3N2O2S, 433; found 433.3.
Workup
- temperatureheated
- temperatureat reflux for 3 h
- customaffording a crystalline product
- filtrationThe resulting suspension was filtered
- washrinsed with HOAc (3×5 mL)
- customthe solids dried in vacuo
Sources & evidence
- ORD record
- ord-71946a0286fe48f99d93a32d8c1a6f77
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318939B2
Reaction notes
Loading…