4-(Methanesulfonyl)phenylboronic acid → 8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 472361Notes

Reaction equation

HRID 472361 reaction equation
Br[C:2]1[C:3]2[N:4]([N:12]=[C:13]([NH2:15])[N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)(=[O:19])=[O:18]>>[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]3[N:4]([N:12]=[C:13]([NH2:15])[N:14]=3)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 674814698-Bromo-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 674814178-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Procedure

8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 8-bromo-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine and (4-methylsulfonylphenyl)boronic acid in a manner analogous to Step 2c to afford a white solid (67%) MP=236-237° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.28 (s, 1H), 8.42 (d, J=7.8 Hz, 2H), 8.07 (s, 1H), 8.06 (d, J=7.8 Hz, 2H), 6.58 (bs, 2H), 3.29 (s, 3H). MS=356.33 (MH)+.

Sources & evidence

ORD record
ord-3b365af49c5f42f3bba909cc890e9f18
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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