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

HRID 478223Notes

Reaction equation

HRID 478223 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([O:15][CH3:16])([O:13][CH3:14])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([C:31]3[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:28]=[CH:29][CH:30]=2)O1>>[CH3:14][O:13][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:29]3[CH:28]=[C:27]([C:31]4[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:26]=[CH:25][CH:30]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([O:15][CH3:16])[CH3:12]

Participants

3

Reactant 2

HCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 180012923-Bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-a]pyrimidine

Product 1

HCID 101780613'-[7-(1,1-Dimethoxyethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrileYield 76%

Procedure

3-Bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-a]pyrimidine (197 mg, 0.50 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′-[7-(1,1-dimethoxyethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile (200 mg, 76%) as a white powder: δH (360 MHz, CDCl3) 1.72 (3H, s), 3.30 (6H, s), 7.39 (1H, d, J 7), 7.49-7.73 (6H, m), 7.78-7.84 (2H, m), 7.97 (1H, s), 8.95 (1H, d, J 7); m/z (ES+) 385 (M++H).

Sources & evidence

ORD record
ord-d4c9d7630ba54fadb6c0f9f864afa9d2
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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