3'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile → 3'-(7-Cyclobutylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 478226Notes

Reaction equation

HRID 478226 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]3[CH2:14][CH2:13][CH2:12]3)=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[C:25]([C:29]3[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:26]=[CH:27][CH:28]=2)O1>>[CH:11]1([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:27]4[CH:26]=[C:25]([C:29]5[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:24]=[CH:23][CH:28]=4)=[CH:3][N:4]=[C:5]3[N:10]=2)[CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 180013033-Bromo-7-cyclobutylimidazo[1,2-a]pyrimidine

Product 1

HCID 99030183'-(7-Cyclobutylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

Procedure

3-Bromo-7-cyclobutylimidazo[1,2-a]pyrimidine was coupled with 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 3′-(7-cyclobutylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile as a white powder: δH (400 MHz, CDCl3) 1.90-2.55 (6H, m), 3.77 (1H, quintet, J 8), 6.83 (1H, d, J 7), 7.48-7.75 (7H, m), 7.82 (1H, dd, J 8 and 1), 7.86 (1H, s), 8.85 (1H, d, J 7); m/z (ES+) 351 (M++H).

Sources & evidence

ORD record
ord-4ff283ec41204511b7737957831078c0
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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