N-(6-bromopyridin-2-yl)acetamide → HCID 9901657, compound

HRID 1796073Notes

Reaction equation

HRID 1796073 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26]([F:29])([F:28])[F:27])=[N:25][C:20]2=[N:19][CH:18]=1)CCC>>[F:28][C:26]([F:27])([F:29])[C:24]1[CH:23]=[CH:22][N:21]2[C:17]([C:2]3[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][CH:3]=3)=[CH:18][N:19]=[C:20]2[N:25]=1

Participants

3

Reactant 2

HCID 10353221N-(6-bromopyridin-2-yl)acetamideHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9901657HCID 9901657, compoundYield 2.8%

Procedure

N-(6-Bromopyridin-2-yl)acetamide (0.33 g, 1.56 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.6 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with ethyl acetate on a gradient of methanol (0-5%) gave N-[6-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)pyridin-2-yl]acetamide (14 mg) as an off-white solid: δH (400 MHz, DMSO) 2.19 (3H, s), 7.60 (1H, d, J 7), 7.85 (1H, d, J 7), 7.92 (1H, dd, J 8 and 8), 7.97 (1H, d, J 8), 8.90 (1H, s), 10.65 (1H, s), 10.75 (1H, d, J 7); m/z (ES+) 321 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with ethyl acetate on a gradient of methanol (0-5%)

Sources & evidence

ORD record
ord-51777ff7c58c4871b864697848c8fa78
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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