3-Bromoimidazo(1,2-a)pyrimidine → 3'-(Imidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 478219Notes

Reaction equation

HRID 478219 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:19]2[CH:20]=[C:21]([C:25]3[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:23][CH:24]=2)O1>>[N:4]1[CH:3]=[C:2]([C:23]2[CH:22]=[C:21]([C:25]3[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:20]=[CH:19][CH:24]=2)[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]=12

Participants

3

Reactant 2

HCID 27638713-Bromoimidazo(1,2-a)pyrimidineHCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Product 1

HCID 98792483'-(Imidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 60%

Procedure

3-Bromoimidazo[1,2-a]pyrimidine (0.29 g, 1.68 mmol) 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′-(imidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile (260 mg, 60%) as an off-white powder: δH (360 MHz, CDCl3) 6.97 (1H, dd, J 7 and 4), 7.51 (1H, td, J 1 and 8), 7.59 (1H, dd, J 7 and 1), 7.62-7.73 (4H, m), 7.77-7.78 (1H, m), 7.82 (1H, dd, J 8 and 1), 7.96 (1H, s), 8.60 (1H, dd, J 7 and 2), 8.98 (1H, d, J 7 and 2); m/z (ES+) 297 (M++H).

Sources & evidence

ORD record
ord-8748b8046a3e4eca868e7abfb83bf16f
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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