Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 6-(7-Trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-2,3'-bipyridine

HRID 1796072Notes

Reaction equation

HRID 1796072 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[N:23]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[N:27][C:22]2=[N:21][CH:20]=1)CCC>>[F:30][C:28]([F:29])([F:31])[C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:2]3[N:7]=[C:6]([C:8]4[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=4)[CH:5]=[CH:4][CH:3]=3)=[CH:20][N:21]=[C:22]2[N:27]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 135464546-Bromo-2,3'-bipyridine

Product 1

HCID 101543706-(7-Trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-2,3'-bipyridineYield 23.8%

Procedure

6-Bromo-2,3′-bipyridine (0.37 g, 1.6 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 dichloromethane on a gradient of methanol (0-5%) and trituration with isohexane gave 6-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)-2,3′-bipyridine (130 mg) as a pale yellow solid: δH (400 MHz, CDCl3) 7.40 (1H, d, J 7), 7.50 (1H, dd, J 8 and 8), 7.72 (1H, d, J 8), 7.85 (1H, d, J 8), 7.97 (1H, dd, J 8 and 8), 8.30 (1H, m), 8.59 (1H, s), 8.75 (1H, m), 9.29 (1H, s), 10.51 (1H, d, J 7); m/z (ES+) 341 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-5%) and trituration with isohexane

Sources & evidence

ORD record
ord-89075c8de95948dcb2bb759af6a434eb
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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