2-Bromo-6-ethoxypyridine → 3-(6-Ethoxypyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796083Notes

Reaction equation

HRID 1796083 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH3:10])[N:3]=1.C([Sn](CCCC)(CCCC)[C:16]1[N:20]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[N:24][C:19]2=[N:18][CH:17]=1)CCC>>[CH2:9]([O:8][C:4]1[N:3]=[C:2]([C:16]2[N:20]3[CH:21]=[CH:22][C:23]([C:25]([F:26])([F:27])[F:28])=[N:24][C:19]3=[N:18][CH:17]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:10]

Participants

3

Reactant 2

HCID 12010182-Bromo-6-ethoxypyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 98796433-(6-Ethoxypyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-alpha]pyrimidineYield 25.8%

Procedure

2-Bromo-6-ethoxypyridine (0.30 g, 1.48 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.13 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-40%) and trituration with isohexane gave 3-(6-ethoxypyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-α]pyrimidine (90 mg) as a pale yellow solid: δH (400 MHz, CDCl3) 1.50 (3H, t, J 7), 4.45 (2H, quartet, J 7), 6.73 (1H, d, J 8), 7.34 (1H, d, J 7), 7.41 (1H, d, J 7), 7.71 (1H, dd, J 8 and 7), 8.46 (1H, s), 10.31 (1H, d, J 7); m/z (ES+) 309 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-40%) and trituration with isohexane

Sources & evidence

ORD record
ord-7a07fd1242784222aa249a54e89b7702
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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