5-(3-Bromo-4-fluorophenyl)-3-methylsulfanyl-[1,2,4]triazine → 3-(3,5-Difluoropyridin-2-yl)-5-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-[1,2,4]triazine

HRID 1064299Notes

Reaction equation

HRID 1064299 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11](SC)[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[F:17][C:18]1[C:19]([Sn](CCCC)(CCCC)CCCC)=[N:20][CH:21]=[C:22]([F:24])[CH:23]=1>>[F:17][C:18]1[C:19]([C:11]2[N:12]=[N:13][CH:14]=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([C:21]4[C:22]([F:24])=[CH:23][C:18]([F:17])=[CH:19][N:20]=4)[CH:3]=3)[N:10]=2)=[N:20][CH:21]=[C:22]([F:24])[CH:23]=1

Participants

3

Reactant 2

HCID 222735835-(3-Bromo-4-fluorophenyl)-3-methylsulfanyl-[1,2,4]triazineHCID 222735933,5-Difluoro-2-tributylstannylpyridine

Product 1

HCID 100465893-(3,5-Difluoropyridin-2-yl)-5-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-[1,2,4]triazine

Procedure

A solution of 5-(3-bromo-4-fluorophenyl)-3-methylsulfanyl-[1,2,4]triazine and 3,5-difluoro-2-tributylstannylpyridine were coupled together by the method of Example 36 to give 3-(3,5-difluoropyridin-2-yl)-5-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-[1,2,4]triazine: δH (500 MHz, CDCl3) 7.38-7.46 (3H, m), 8.44-8.48 (1H, m), 8.50 (1H, dd, J 2.3, 6.7 Hz), 8.52 (1H, d, J 2.3 Hz), 8.63 (1H, s), 9.77 (1H, s); m/z (ES+) 402.

Sources & evidence

ORD record
ord-2e2fe426bb93414aac610f23db0edffb
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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