2-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 10269701, compound

HRID 1796040Notes

Reaction equation

HRID 1796040 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([CH3:19])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31]#[N:32])O1>>[F:20][C:17]([C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:6]3[N:7]=[C:2]([C:29]4[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=4[C:31]#[N:32])[CH:3]=[CH:4][CH:5]=3)=[CH:9][N:10]=[C:11]2[N:16]=1)([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 9945633HCID 9945633, compound

Product 1

HCID 10269701HCID 10269701, compoundYield 37%

Procedure

The product of Example 25 (0.34 g, 1.0 mmol) was coupled to 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile following the procedure in Example 2 to give 2-{6-[7-(1-fluoro-1-methyl-ethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile (0.133 g, 37%) as a white solid: δH (360 MHz, CDCl3) 1.80 (6H, d, J 22), 7.38 (1H, dd, J 7 and 2), 7.59 (1H, ddd, J 8, 7 and 1), 7.75 (1H, ddd, J 8, 7 and 1), 7.80-7.96 (5H, m), 8.38 (1H, s), 10.36 (1H, d, J 7); m/z (ES+) 358 (M++H).

Sources & evidence

ORD record
ord-c08b667c28134f36b4f69daea98c060e
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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