2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → 5'-[7-Chloro-8-fluoroimidazo[1,2-alpha]pyridin-3-yl]-2'-fluorobiphenyl-2-carbonitrile

HRID 1180228Notes

Reaction equation

HRID 1180228 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([Cl:12])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][C:15]=1[C:29]1[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=1>>[Cl:12][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[C:15]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:16]=3)=[CH:3][N:4]=[C:5]2[C:10]=1[F:11]

Participants

3

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 695617863-Bromo-7-chloro-8-fluoroimidazo[1,2-a]pyridine

Product 1

HCID 104289345'-[7-Chloro-8-fluoroimidazo[1,2-alpha]pyridin-3-yl]-2'-fluorobiphenyl-2-carbonitrileYield 71%

Procedure

3-Bromo-7-chloro-8-fluoroimidazo[1,2-α]pyridine (70 mg, 0.28 mmol) was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (109 mg, 0.34 mmol), as described in Example 1, to afford the title compound as a white amorphous solid (72 mg, 71%): δH (400 MHz, DMSO) 7.11 (1H, t, J 7.0), 7.60-7.70 (2H, m), 7.78 (1H, s), 7.85-7.89 (3H, m), 7.93 (1H, s), 8.04 (1H, dd, J 0.8, 7.8), 8.52 (1H, dd, J 1.0, 7.2); m/z (ES+) 366 (100%, [MH]+).

Sources & evidence

ORD record
ord-403490a7e66244328f9c7bfa12b821ec
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

Loading…