2-Bromopyridine → 7-Methyl-3-[3-(pyridin-2-yl)phenyl]imidazo[1,2-a]pyrimidine

HRID 478242Notes

Reaction equation

HRID 478242 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13](B4OC(C)(C)C(C)(C)O4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[N:3]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 180012787-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyrimidine

Product 1

HCID 98355457-Methyl-3-[3-(pyridin-2-yl)phenyl]imidazo[1,2-a]pyrimidineYield 36.1%

Procedure

7-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)phenyl]-imidazo[1,2-a]pyrimidine (0.1 g, 0.29 mmol) was coupled to 2-bromopyridine (55 μl, 0.59 mmol) as described in Example 26 to give 7-methyl-3-[3-(pyridin-2-yl)phenyl]imidazo[1,2-a]pyrimidine as a white solid (30 mg): δH (400 MHz, CDCl3) 2.67 (3H, s), 6.79 (1H, d, J 7), 7.30 (1H, m 7.55-7.65 (2H, m), 7.77-7.81 (2H, m), 7.87 (1H, s), 8.00 (1H, dd, J 8 and 1.6), 8.19 (1H, d, J 1.5), 8.57 (1H, d, J 7), 8.71 (1H, d, J 1.6); m/z (ES+) 287 (M++H).

Sources & evidence

ORD record
ord-787bc55ebf914791aa8057bdf795038a
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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