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

HRID 1064297Notes

Reaction equation

HRID 1064297 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](CCCC)(CCCC)CCCC)=[N:26][CH:27]=[CH:28][CH:29]=1>>[F:8][C:7]1[CH:6]=[CH:5][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:3][C:2]=1[C:25]1[C:24]([F:23])=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

3

Reactant 2

HCID 99985945-(3-Bromo-4-fluorophenyl)-3-(4-methoxyphenyl)-[1,2,4]triazineHCID 164271503-Fluoro-2-(tributylstannyl)pyridine

Product 1

HCID 100681035-[4-Fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-(4-methoxyphenyl)-[1,2,4]triazineYield 38%

Procedure

5-(3-Bromo-4-fluorophenyl)-3-(4-methoxyphenyl)-[1,2,4]triazine (100 mg, 0.28 mmol) was coupled to 3-fluoro-2-tributylstannylpyridine (129 mg, 0.33 mmol) using the method described in Example 22 to give 5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-(4-methoxyphenyl)-[1,2,4]triazine as a pale yellow solid (40 mg): δH (400 MHz, CDCl3) 3.91 (3H, s), 7.04-7.08 (2H, m), 7.39-7.47 (2H, m), 7.56-7.61 (1H, m), 8.41-8.45 (1H, m), 8.54 (1H, dd, J 2.3, 6.7 Hz), 8.60-8.64 (3H, m), 9.57 (1H, s); m/z (ES+) 377.

Sources & evidence

ORD record
ord-59a0faf5196740e5981a477467e4bb99
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

Loading…