2,2,2-Trifluoroethanesulfonyl chloride → 2,2,2-trifluoro-ethanesulfonic acid [5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide

HRID 1630925Notes

Reaction equation

HRID 1630925 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[C:13]([CH2:17][NH2:18])[CH:14]=[N:15][CH:16]=1.[F:19][C:20]([F:27])([F:26])[CH2:21][S:22](Cl)(=[O:24])=[O:23]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[C:13]([CH2:17][NH:18][S:22]([CH2:21][C:20]([F:27])([F:26])[F:19])(=[O:24])=[O:23])[CH:14]=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 58215711C-[5-(1-Methyl-1H-indol-2-yl)-pyridin-3-yl]-methylamine

Product 1

HCID 582157652,2,2-trifluoro-ethanesulfonic acid [5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide

Procedure

C-[5-(1-Methyl-1H-indol-2-yl)-pyridin-3-yl]-methylamine (Example 200b) and 2,2,2-trifluoro-ethanesulfonyl chloride are processed according to the method described in Example 186f to give 2,2,2-trifluoro-ethanesulfonic acid [5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-amide. 1H NMR (400 MHz, MeOD) δ ppm 3.78 (s, 3H), 4.23 (q, J=9.6 Hz, 2H), 4.44 (s, 2H), 6.66 (d, J=0.5 Hz, 1H), 7.06-7.12 (m, 1H), 7.23 (ddd, J=7.7, 1.1 Hz, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.58 (d, J=7.8 Hz, 1H), 8.04 (t, J=2.0 Hz, 1H), 8.56 (d, J=2.0 Hz, 1H), 8.68 (d, J=1.9 Hz, 1H). HRMS (ESI) m/z 384.0999 [(M+H)+ Calcd for C17H17F3N3O2S: 384.0994].

Sources & evidence

ORD record
ord-d4557c90607d47d0992772b6c99d558c
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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