Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 69707978, compound

HRID 2184050Notes

Reaction equation

HRID 2184050 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2[CH:15]=[N: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[CH:15]=[N: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 22473572HCID 22473572, compound

Product 1

HCID 69707978HCID 69707978, compound

Procedure

3-(5-Bromo-2-fluorophenyl)isonicotinonitrile (40 mg, 0.14 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.18 mmol) by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 3% methanol, then recrystallisation from toluene/isohexane, gave 3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]isonicotinonitrile as a yellow solid: δH (400 MHz, CDCl3) 7.30 (1H, d, J 7), 7.51 (1H, t, J 9), 7.67-7.73 (3H, m), 8.13 (1H, s), 8.87 (1H, d, J 5), 8.96-8.98 (2H, m); m/z (ES+) 384 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 3% methanol
  2. customrecrystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-6bde2616e3764f25b687028e0a8859b3
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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