2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10199642, compound

HRID 2183884Notes

Reaction equation

HRID 2183884 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F: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[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=1>>[F:13][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[C:17]([C:31]4[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:18]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([F:14])[CH3:12]

Participants

3

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 69709942HCID 69709942, compound

Product 1

HCID 10199642HCID 10199642, compoundYield 24%

Procedure

3-Bromo-7-(1,1-difluoroethyl)imidazo[1,2-α]pyrimidine (130 mg, 0.50 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-(1,1-difluoroethyl)imidazo[1,2-α]pyrimidin-3-yl]-2′-fluorobiphenyl-2-carbonitrile (45 mg, 24%) as a white powder: δH (400 MHz, CDCl3) 2.15 (3H, t, J 21), 7.34 (1H, d, J 7), 7.43 (1H, t, J 9), 7.53-7.74 (5H, m), 7.86 (1H, dd, J 8 and 1), 7.99 (1H, s), 8.95 (1H, d, J 7); m/z (ES+) 379 (M++H).

Sources & evidence

ORD record
ord-13f71430a3214f98bfed49848bf1e23d
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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