Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 2-[2-Fluoro-5-(7-trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)phenyl]nicotinonitrile

HRID 2183956Notes

Reaction equation

HRID 2183956 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[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[N:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 222852972-(5-Bromo-2-fluorophenyl)nicotinonitrile

Product 1

HCID 102215442-[2-Fluoro-5-(7-trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)phenyl]nicotinonitrile

Procedure

2-(5-Bromo-2-fluorophenyl)nicotinonitrile (214 mg, 0.8 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.1 mmol) by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol, then crystallisation from toluene, gave 2-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]nicotinonitrile as a yellow solid: δH (400 MHz, CDCl3) 8.95 (1H, dd, J 5 and 2), 8.91 (1H, d, J 7), 8.17 (1H, dd, J 8 and 2), 8.13 (1H, s), 7.80 (1H, dd, J 7 and 2), 7.69-7.73 (1H, m), 7.46-7.55 (2H, m), 7.29 (1H, d, J 7); m/z (ES+) 383 (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-213cbdc0c7604588bdf907bc16cf415b
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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