3-Fluoro-2-(tributylstannyl)pyridine → 5-[4-Fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-(3-fluoropyridin-2-yl)-[1,2,4]triazine

HRID 1064298Notes

Reaction equation

HRID 1064298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10](SC)[N:11]=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=1.[F:23][C:24]1[C:25]([Sn](CCCC)(CCCC)CCCC)=[N:26][CH:27]=[CH:28][CH:29]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:25]3[C:24]([F:23])=[CH:29][CH:28]=[CH:27][N:26]=3)[N:11]=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

3

Reactant 2

HCID 164271503-Fluoro-2-(tributylstannyl)pyridineHCID 222735905-[4-Fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine

Product 1

HCID 100443575-[4-Fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-(3-fluoropyridin-2-yl)-[1,2,4]triazineYield 12%

Procedure

5-[4-Fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine (100 mg, 0.32 mmol) was coupled to 3-fluoro-2-tributylstannylpyridine (146 mg, 0.38 mmol) using the method described in Example 36 to give 5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-(3-fluoropyridin-2-yl)-[1,2,4]triazine as a yellow solid (14 mg): δH (400 MHz, CDCl3) 7.38-7.46 (2H, m), 7.52-7.60 (2H, m), 7.64-7.70 (1H, m), 8.44-8.48 (1H, m), 8.54 (1H, dd, J 2.3, 6.7 Hz), 8.59-8.61 (1H, m), 8.71 (1H, d, J 4.3 Hz), 9.79 (1H, s); m/z (ES+) 366.

Sources & evidence

ORD record
ord-7589265253e642ddbfff332aa26af325
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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