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

HRID 478225Notes

Reaction equation

HRID 478225 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[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>>[C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:27]3[CH:26]=[C:25]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:24]=[CH:23][CH:28]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 180012873-Bromo-7-tert-butylimidazo[1,2-a]pyrimidine

Product 1

HCID 102916183'-(7-Tert-butylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

Procedure

3-Bromo-7-tert-butylimidazo[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-tert-butylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile as an off-white powder: Found C, 77.17; H, 5.79; N, 15.78. C23H20N4.0.3(H2O) requires C, 77.21; H, 5.80; N, 15.66; δH (400 MHz, CDCl3) 1.44 (9H, s), 7.05 (1H, d, J 7), 7.48-7.76 (7H, m), 7.83 (1H, dd, J 8 and 1), 7.86 (1H, s), 8.88 (1H, d, J 7); m/z (ES+) 353 (M++H).

Sources & evidence

ORD record
ord-c19d0f60148c445d85207a372e79a792
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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