Trifluoromethanesulfonyl chloride → HCID 58215761, compound

HRID 1630929Notes

Reaction equation

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

Participants

Reactant 2

HCID 79000Trifluoromethanesulfonyl chloride

HCID 58215661HCID 58215661, compound

Product 1

HCID 58215761HCID 58215761, compound

Procedure

C-[5-(6-Chloro-1-methyl-1H-indol-2-yl)-pyridin-3-yl]-methylamine (Example 205a) and trifluoromethanesulfonyl chloride are processed according to the method described in Example 186f to give C,C,C-trifluoro-N-[5-(6-chloro-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-methanesulfonamide. 1H NMR (400 MHz, MeOD) δ ppm 3.80 (s, 3H), 4.59 (s, 2H), 6.72 (s, 1H), 7.12 (dd, J=8.5, 1.9 Hz, 1H), 7.54 (s, 1H), 7.60 (d, J=8.6 Hz, 1H), 8.05 (t, J=2.1 Hz, 1H), 8.63 (d, J=2.0 Hz, 1H), 8.76 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 404.0443 [(M+H)+ Calcd for C16H14ClF3N3O2S: 404.0447].

Sources & evidence

ORD record: ord-eced3490f1754908ab8412a4d210fbc0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791141B2

Reaction notes

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