3-(Diethylboryl)pyridine → 5-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine

HRID 1064280Notes

Reaction equation

HRID 1064280 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([S:15][CH3:16])[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(B(CC)[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)C>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:10]=[C:11]([S:15][CH3:16])[N:12]=[N:13][CH:14]=2)=[CH:3][C:2]=1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 6428513-(Diethylboryl)pyridineHCID 222735835-(3-Bromo-4-fluorophenyl)-3-methylsulfanyl-[1,2,4]triazine

Product 1

HCID 222735955-[4-Fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine

Procedure

5-(3-Bromo-4-fluorophenyl)-3-methylsulfanyl-[1,2,4]triazine was coupled to diethyl(3-pyridyl)borane by the method of Example 12 to give 5-[4-fluoro-3-(pyridin-3-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine as a yellow solid: δH (400 MHz, CDCl3) 2.74 (3H, s), 7.37-7.46 (2H, m), 7.91-7.95 (1H, m), 8.16-8.20 (1H, m), 8.30 (1H, dd, J 2.3, 7.4 Hz), 8.70 (1H, dd, J 1.4, 4.9 Hz), 8.86 (1H, s), 9.40 (1H, s); m/z (ES+) 299.

Sources & evidence

ORD record
ord-95f4405e4c6544c38a648563f4c65ef3
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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