2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → HCID 10178861, compound

HRID 2183891Notes

Reaction equation

HRID 2183891 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[O:15][N:14]=[C:13]([CH3:16])[N:12]=3)=[N:10][C:5]2=[N:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][C:19]=1[C:33]1[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]4[O:15][N:14]=[C:13]([CH3:16])[N:12]=4)=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:20][C:19]=1[C:33]1[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=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 69708695HCID 69708695, compound

Product 1

HCID 10178861HCID 10178861, compound

Procedure

3-Bromo-7-(3-methyl-[1,2,4]oxadiazol-5-yl)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 as described in Example 2 to give 2′-fluoro-5′-[7-(3-methyl-[1,2,4]oxadiazol-5-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile as a yellow solid: δH (400 MHz, CDCl3) 2.55 (3H, s), 7.46 (1H, t, J 9), 7.56-7.59 (1H, m), 7.64 (2H, dd, J 7 and 2), 7.69-7.73 (2H, m), 7.81-7.87 (2H, m), 8.16 (1H, s), 9.05 (1H, s); m/z (ES+) 397 (M++H).

Sources & evidence

ORD record
ord-ccedfbd23bdb444aa53841ed48480bc9
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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