2-(4-Chloro-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-(4-Chloro-2-fluorophenyl)-5-[4-fluoro-3-(3-fluoro-pyridin-2-yl)phenyl]-[1,2,4]triazine

HRID 1064300Notes

Reaction equation

HRID 1064300 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.[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[C:26]([F:39])[CH:25]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:10]2[N:11]=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:16]4[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH:4]=3)[N:9]=2)=[C:26]([F:39])[CH:25]=1

Participants

3

Reactant 2

HCID 222735882-(4-Chloro-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 222735905-[4-Fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine

Product 1

HCID 100238273-(4-Chloro-2-fluorophenyl)-5-[4-fluoro-3-(3-fluoro-pyridin-2-yl)phenyl]-[1,2,4]triazine

Procedure

A solution of 5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine and 2-(4-chloro-2-fluorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane were coupled together by the method of Example 2 to give 3-(4-chloro-2-fluorophenyl)-5-[4-fluoro-3-(3-fluoro-pyridin-2-yl)phenyl]-[1,2,4]triazine: δH (500 MHz, CDCl3) 7.30-7.35 (2H, m), 7.40-7.46 (2H, m), 7.53-7.61 (1H, m), 8.26 (1H, t, J8.2 Hz), 8.42-8.45 (1H, m), 8.54 (1H, dd, J 2.4, 6.6 Hz), 8.62 (1H, d, J 4.6 Hz), 9.69 (1H, s); m/z (ES+) 399.

Sources & evidence

ORD record
ord-eb77b3deaf754f1080844293e4e0386c
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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