3'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile → HCID 9946617, compound

HRID 478235Notes

Reaction equation

HRID 478235 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11](Br)=[CH:12][N:13]=[C:7]2[N:6]=1)=[O:4].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>>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:27]3[CH:26]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]#[N:36])[CH:24]=[CH:23][CH:28]=3)=[CH:12][N:13]=[C:7]2[N:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 70026105Methyl 3-bromoimidazo[1,2-a]pyrimidine-7-carboxylate

Product 1

HCID 9946617HCID 9946617, compound

Procedure

3-Bromoimidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester 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-(2′-cyanobiphenyl-3-yl)-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester as a pale yellow powder: δH (400 MHz, CDCl3) 4.07 (3H, s), 7.50-7.54 (1H, m), 7.58-7.76 (6H, m), 7.81-7.84 (2H, m), 8.18 (1H, s), 9.10 (1H, d, J 7); m/z (ES+) 355 (M++H).

Sources & evidence

ORD record
ord-64de25b87a6c46febcb107a4a937cb30
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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