Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 69708353, compound

HRID 2184043Notes

Reaction equation

HRID 2184043 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[N:9]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:22]1[N:26]2[CH:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[N:30][C:25]2=[N:24][CH:23]=1)CCC>>[F:16][C:5]1[CH:4]=[CH:3][C:2]([C:22]2[N:26]3[CH:27]=[CH:28][C:29]([C:31]([F:32])([F:33])[F:34])=[N:30][C:25]3=[N:24][CH:23]=2)=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[N:9]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22473554HCID 22473554, compound

Product 1

HCID 69708353HCID 69708353, compound

Procedure

2-(5-Bromo-2-fluorophenyl)-6-methoxypyridine (595 mg, 2.1 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazol[1,2-α]pyrimidine (3.2 mmol) by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol, then crystallisation from methanol, gave 3-[4-fluoro-3-(6-methoxypyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 3.98 (3H, s), 6.79 (1H, d, J 8), 7.26 (1H, d, J 10), 7.38 (1H, dd, J 11 and 9), 7.52-7.56 (2H, m), 7.70 (1H, t, J 8), 8.12 (1H, s), 8.36 (1H, dd, J 7 and 2), 8.85 (1H, d, J 7).

Workup

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

Sources & evidence

ORD record
ord-5f21425b4509454f87036f096d034fc5
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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