Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 3-[6-(Pyrrolidin-1-yl)pyridin-2-yl]-7-trifluoromethylimidazo[1,2-alpha]pyrimidine

HRID 1796016Notes

Reaction equation

HRID 1796016 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]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)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 154702772-Bromo-6-(pyrrolidin-1-yl)pyridine

Product 1

HCID 99455273-[6-(Pyrrolidin-1-yl)pyridin-2-yl]-7-trifluoromethylimidazo[1,2-alpha]pyrimidineYield 26.8%

Procedure

2-Bromo-6-(pyrrolidin-1-yl)pyridine (481 mg, 2.1 mmol) (prepared by the method of T. Sammakia et al., J. Org. Chem., 1999, 64(13), 4652-4664) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.4 mmol) by the method of Example 1 to give 3-[6-(pyrrolidin-1-yl)pyridin-2-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (125 mg) as a white solid: δH (360 MHz, DMSO) 2.02 (4H, t, J 6.5), 3.51 (4H, bs), 6.43 (1H, d, J 8.4), 7.27 (1H, d, J 7.7), 7.63 (1H, t, J 7.9), 7.71 (1H, d, J 7.4), 8.72 (1H, s), 10.51 (1H, d, J 7.4); m/z (ES+) 334 (M++H).

Sources & evidence

ORD record
ord-0214cb4ea6c045148041e4e3a15e070b
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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