2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → 5'-(7-Difluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-2'-fluorobiphenyl-2-carbonitrile

HRID 2183885Notes

Reaction equation

HRID 2183885 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][C:16]=1[C:30]1[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=1>>[F:12][CH:11]([F:13])[C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:18]3[CH:19]=[CH:20][C:15]([F:14])=[C:16]([C:30]4[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:17]=3)=[CH:3][N:4]=[C:5]2[N:10]=1

Participants

3

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 180012863-Bromo-7-difluoromethylimidazo[1,2-a]pyrimidine

Product 1

HCID 99690295'-(7-Difluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-2'-fluorobiphenyl-2-carbonitrileYield 49%

Procedure

3-Bromo-7-difluoromethylimidazo[1,2-α]pyrimidine (248 mg, 1.00 mmol) was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 5′-(7-difluoromethylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile (180 mg, 49%) as a yellow powder: δH (400 MHz, CDCl3) 6.66 (1H, t, J 55), 7.29 (1H, d, J 7), 7.44 (1H, t, J 9), 7.54-7.74 (5H, m), 7.87 (1H, dd, J 8 and 1), 8.02 (1H, s), 9.00 (1H, d, J 7); m/z (ES+) 365 (M++H).

Sources & evidence

ORD record
ord-0747b7c26fd04947af371dfbfe9d8da7
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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