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

HRID 2183876Notes

Reaction equation

HRID 2183876 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F: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[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=1>>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([F:14])([CH3:13])[CH3:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:18][C:17]=1[C:31]1[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=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 695605543-Bromo-7-(1-fluoro-1-methylethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 102707422'-Fluoro-5'-[7-(1-fluoro-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]biphenyl-2-carbonitrile

Procedure

3-Bromo-7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidine was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile in the same way as described for Example 1 to give 2′-fluoro-5′-[7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile as an off-white solid: δH (360 MHz, DMSO) 1.76 (6H, d, J 22), 7.27 (1H, dd, J 6 and 1), 7.64-7.72 (2H, m), 7.80 (1H, s), 7.89-7.92 (3H, m), 8.04 (1H, s), 8.06 (1H, s), 9.15 (1H, d, J 7); m/z (ES+) 375 (M++H).

Sources & evidence

ORD record
ord-5c0b08a8238142fa840ed60dd2d9f426
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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