5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine → 3-(2,4-Difluorophenyl)-5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-[1,2,4]triazine

HRID 1064296Notes

Reaction equation

HRID 1064296 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]([F:21])=[CH:17][C:16]=3[F:22])[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[F:23][C:24]1[C:25]([Sn](CCCC)(CCCC)CCCC)=[N:26][CH:27]=[CH:28][CH:29]=1>>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C:11]1[N:12]=[N:13][CH:14]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([C:25]3[C:24]([F:23])=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:3]=2)[N:10]=1

Participants

3

Reactant 2

HCID 103842555-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazineHCID 164271503-Fluoro-2-(tributylstannyl)pyridine

Product 1

HCID 117405943-(2,4-Difluorophenyl)-5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-[1,2,4]triazineYield 58.1%

Procedure

5 5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine (100 mg, 0.27 mmol) was coupled to 3-fluoro-2-tributylstannylpyridine (127 mg, 0.33 mmol) using the method described in Example 22 to give 3-(2,4-difluorophenyl)-5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-[1,2,4]triazine as a pale yellow solid (60 mg): δH (400 MHz, CDCl3) 6.99-7.10 (2H, m), 7.39-7.47 (2H, m), 7.56-7.61 (1H, m), 8.29-8.36 (1H, m), 8.41-8.45 (1H, m), 8.53 (1H, dd, J 2.3, 6.7 Hz), 8.60-8.63 (1H, m), 9.68 (1H, s); m/z (ES+) 383.

Sources & evidence

ORD record
ord-ddd06bc91b2547c494668f11747ed439
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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