Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 10132405, compound

HRID 1796079Notes

Reaction equation

HRID 1796079 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[N:10][S:11][CH:12]=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>>[S:11]1[CH:12]=[C:8]([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:9]=[N:10]1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22180765HCID 22180765, compound

Product 1

HCID 10132405HCID 10132405, compoundYield 33.1%

Procedure

2-Bromo-6-(isothiazol-4-yl)pyridine (0.27 g, 1.13 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 (20-80%) and trituration with isohexane gave 3-[6-(isothiazol-4-yl)pyridin-2-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (130 mg) as a pale yellow solid: δH (400 MHz, CDCl3) 7.41 (1H, d, J 7), 7.62 (1H, d, J 8), 7.78 (1H, d, J 8), 7.92 (1H, dd, J 8 and 8), 8.56 (1H, s), 9.12 (1H, s), 9.13 (1H, s), 10.45 (1H, d, J 7); m/z (ES+) 347 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-80%) and trituration with isohexane

Sources & evidence

ORD record
ord-10521c869a7a402298ec6faefda62954
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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