Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 9858693, compound

HRID 1796066Notes

Reaction equation

HRID 1796066 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[N:22]2[CH:23]=[CH:24][C:25]([C:27]([F:30])([F:29])[F:28])=[N:26][C:21]2=[N:20][CH:19]=1)CCC>>[N:8]1([C:4]2[N:3]=[C:2]([C:18]3[N:22]4[CH:23]=[CH:24][C:25]([C:27]([F:28])([F:29])[F:30])=[N:26][C:21]4=[N:20][CH:19]=3)[CH:7]=[CH:6][CH:5]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 221807822-Bromo-6-(1H-imidazol-1-yl)pyridine

Product 1

HCID 9858693HCID 9858693, compoundYield 15.9%

Procedure

2-Bromo-6-(1H-imidazol-1-yl)pyridine (0.18 g, 0.8 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.9 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-10%) and trituration with ethyl acetate gave 3-[6-(1H-imidazol-1-yl)pyridin-2-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (42 mg) as an off-white solid: δH (400 MHz, CDCl3) 7.30 (1H, s), 7.35 (1H, d, J 8), 7.43 (1H, d, J 7), 7.65 (1H, s), 7.79 (1H, d, J 8), 8.00 (1H, dd, J 8 and 8), 8.38 (1H, s), 8.59 (1H, s), 10.24 (1H, d, J 7); m/z (ES+) 331 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-10%) and trituration with ethyl acetate

Sources & evidence

ORD record
ord-ee0f4a2593f542b1a390b1774c42b1cd
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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