3-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine → 3-tert-Butyl-7-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-b][1,2,4]triazine

HRID 586251Notes

Reaction equation

HRID 586251 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:17]=1[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1>>[C:11]([C:9]1[CH:8]=[N:7][N:6]2[C:2]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[C:17]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH:18]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 223295217-Bromo-3-tert-butylimidazo[1,2-b][1,2,4]triazine

Product 1

HCID 101324143-tert-Butyl-7-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-b][1,2,4]triazineYield 48%

Procedure

This compound was prepared in 48% yield as described in the final paragraph of Example 2, step d, but using 7-bromo-3-tert-butylimidazo[1,2-b][1,2,4]triazine instead of 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine, and using 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine (prepared as described in Example 3, step f) instead of 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile: 1H NMR (360 MHz, CDCl3) δ 1.50 (9H, s), 7.34 (1H, m), 7.44 (1H, dd, J 4.9, 8.1 Hz), 7.94-8.02 (2H, m), 8.19 (1H, dd, J 2.5, 7.4 Hz), 8.21 (1H, s), 8.59 (1H, s), 8.66 (1H, d, J 4.82 Hz), 8.88 (1H, s); MS (ES+) m/z 348 [M+H]+. Anal. Found: C, 66.95; H, 5.15; N, 19.00%. Required for C20H18FN5.0.75H2O: C, 66.56; H, 5.45; N, 19.41%.

Workup

  1. customThis compound was prepared in 48% yield

Sources & evidence

ORD record
ord-751f7f51bdec47149f05e1b1f0eab69e
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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