3-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine → 7-[6-Fluoro-2'-(methanesulfonyl)biphenyl-3-yl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine

HRID 586274Notes

Reaction equation

HRID 586274 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:31])(=[O:30])=[O:29])=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][CH:17]=1.FC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1C1C=NC=CC=1>>[F:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:31])(=[O:30])=[O:29])=[CH:20][C:19]([C:2]2[N:6]3[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 22285323HCID 22285323, compound

Product 1

HCID 101601697-[6-Fluoro-2'-(methanesulfonyl)biphenyl-3-yl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazineYield 89%

Procedure

This was prepared in 89% yield by a similar procedure to that described in Example 3, step f, except using 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine and 2-(6-fluoro-2′-(methanesulfonyl)biphenyl-3-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane instead of 7-bromo-3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine and 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine: 1H NMR (360 MHz, CDCl3) δ 2.93 (3H, s), 7.37 (1H, td, J 1.6, 7.5 Hz), 7.47 (1H, dd, J 1.2, 7.4 Hz), 7.69 (1H, td, J 1.5, 7.8 Hz), 7.75 (1H, td, J 1.5, 7.4 Hz), 8.17-8.21 (2H, m), 8.27 (1H, dd, J 1.4, 8.0 Hz), 8.61 (1H, s), 8.78 (1H, s); MS (ES+) m/z 437 [M+H]+. Anal. Found: C, 52.15; H, 2.85; N, 12.74%. Required for C19H12F4N4O2S: C, 52.29; H, 2.77; N, 12.84%.

Workup

  1. customThis was prepared in 89% yield by a similar procedure to

Sources & evidence

ORD record
ord-153294d0d4d946fca08691c5fbd67ed5
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

Loading…