2-Bromo-5-(trifluoromethyl)pyridine → HCID 9902123, compound

HRID 1796023Notes

Reaction equation

HRID 1796023 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N: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[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=3)=[CH:18][N:19]=[C:20]2[N:25]=1

Participants

3

Reactant 2

HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9902123HCID 9902123, compound

Procedure

2-Bromo-5-trifluoromethylpyridine (1.70 g, 7.5 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (3.8 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol, then crystallisation from toluene, gave 7-trifluoromethyl-3-(5-trifluoromethylpyridin-2-yl)imidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 10.52 (1H, d, J 7), 8.94-8.97 (1H, m), 8.63 (1H, s), 8.03-8.07 (1H, m), 7.96 (1H, d, J 9), 7.41 (1H, d, J 7); m/z (ES+) 333 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 1% methanol
  2. customcrystallisation from toluene

Sources & evidence

ORD record
ord-a26d55083cd74ca587e53dffd3ec47fb
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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