Trifluoromethylsulfonamide → Trifluoromethanesulfonic acid [5-(3-cyano-1-methyl-1h-indol-2-yl)-pyridin-3-ylmethyl]-amide
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH3:20])[C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]=[N:7][CH:8]=1)=O.[F:21][C:22]([F:28])([F:27])[S:23]([NH2:26])(=[O:25])=[O:24]>>[C:18]([C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:20])[C:9]=1[C:5]1[CH:4]=[C:3]([CH2:1][NH:26][S:23]([C:22]([F:28])([F:27])[F:21])(=[O:25])=[O:24])[CH:8]=[N:7][CH:6]=1)#[N:19]Participants
3
Procedure
2-(5-Formyl-pyridin-3-yl)-1-methyl-1H-indole-3-carbonitrile (Example 127) and trifluoromethanesulfonamide are processed according to the method described in Example 170 to give trifluoromethanesulfonic acid [5-(3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]amide. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.79 (s, 3H), 4.58 (s, 2H), 7.34-7.39 (m, 1H), 7.42-7.47 (m, 1H), 7.72 (d, J=7.7 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 8.10 (t, J=2.1 Hz, 1H), 8.78 (d, J=2.1 Hz, 1H), 8.85 (d, J=2.1 Hz, 1H), 10.19 (br. s., 1H). HRMS (ESI) m/z 395.0779 [(M+H)+ Calcd for C17H14F3N4O2S: 395.0790].
Sources & evidence
- ORD record
- ord-c54b017b709b4fdcbdd0c3578a22754b
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030334B2
Reaction notes
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