1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide → 1-[3-((4-(4-Fluoro-2-methoxyphenyl)pyridin-2-yl)amino)phenyl]-N,N-dimethylmethanesulfonamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[O:29][CH3:30])[CH:19]=[CH:18][N:17]=1>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[CH:21]=[CH:16][N:17]=[C:18]([NH:1][C:2]3[CH:3]=[C:4]([CH2:8][S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=3)[CH:19]=2)=[C:23]([O:29][CH3:30])[CH:24]=1Participants
Conditions
- Temperature
- 140 °C
Procedure
The title compound G3 was prepared from 1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide (400 mg, 1.87 mmol) and intermediate A2 (532 mg, 2.24 mmol) following the procedure reported for G1 by heating the reaction mixture for 2 h at 140° C. in a microwave oven. The desired product G3 was obtained by flash chromatography on silica gel (cHex/EtOAc 80:20 to 20:80) as a white solid (274 mg, 35%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 2.71 (s, 6H), 3.81 (s, 3H), 4.34 (s, 2H), 6.82 (dd, J=5.3 Hz, J=1.5 Hz, 1H), 6.88 (dt, J=8.3 Hz, J=1.5 Hz, 1H), 6.91 (d, J=8.0 Hz, 1H), 6.95 (s, 1H), 7.05 (dd, J=11.4 Hz, J=2.4 Hz, 1H), 7.25 (t, J=7.8 Hz, 1H), 7.38 (dd, J=8.3 Hz, J=7.0 Hz, 1H), 7.67 (s, 1H), 7.72 (d, J=8.3 Hz, 1H), 8.14 (d, J=5.3 Hz, 1H), 9.11 (s, 1H). MS (ES) C21H22FN3O3S requires: 415. found: 416 (M+H)+.
Workup
- customwas obtained by flash chromatography on silica gel (cHex/EtOAc 80:20 to 20:80) as a white solid (274 mg, 35%)
Sources & evidence
- ORD record
- ord-1115066399e5473ab370fdc11bc1004c
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242937B2
Reaction notes
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