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

HRID 1064273Notes

Reaction equation

HRID 1064273 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[F:23][C:24]1[C:25]([Sn](C)(C)C)=[N:26][CH:27]=[C:28]([F:30])[CH:29]=1>>[F:23][C:24]1[C:25]([C:2]2[CH:3]=[C:4]([C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[N:12]=[N:13][CH:14]=3)[CH:5]=[CH:6][C:7]=2[F:8])=[N:26][CH:27]=[C:28]([F:30])[CH:29]=1

Participants

3

Reactant 2

HCID 99985945-(3-Bromo-4-fluorophenyl)-3-(4-methoxyphenyl)-[1,2,4]triazineHCID 115872043,5-Difluoro-2-trimethylstannylpyridine

Product 1

HCID 103184565-[3-(3,5-Difluoropyridin-2-yl)-4-fluorophenyl]-3-(4-methoxyphenyl)-[1,2,4]triazine

Procedure

5-(3-Bromo-4-fluorophenyl)-3-(4-methoxyphenyl)-[1,2,4]triazine was coupled to 3,5-difluoro-2-trimethylstannylpyridine using the method of Example 6 to give 5-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-3-(4-methoxyphenyl)-[1,2,4]triazine, crystallised from hot 2-propanol as a pale yellow solid: δH (500 MHz, d6-DMSO) 3.88 (3H, s), 7.17 (2H, d, J 9.0 Hz), 7.69 (1H, t, J 9.1 Hz), 8.20 (1H, m), 8.52 (2H, d, J 9.0 Hz), 8.65-8.70 (2H, m), 8.77 (1H, d, J 2.2 Hz), 10.02 (1H, s); m/z (ES+) 395.

Sources & evidence

ORD record
ord-f795d68856b845a2a6c86a21e01ea5f7
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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