Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 10271284, compound

HRID 2183978Notes

Reaction equation

HRID 2183978 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2[C:9]([C:14]#[N:15])=[N:10][CH:11]=[CH:12][CH:13]=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[C:9]([C:14]#[N:15])=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22473547HCID 22473547, compound

Product 1

HCID 10271284HCID 10271284, compound

Procedure

3-(5-Bromo-2-fluorophenyl)pyridine-2-carbonitrile was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 4% methanol, then crystallisation from hot toluene, gave 3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]pyridine-2-carbonitrile: δH (400 MHz, DMSO) 9.39 (1H, d, J 7), 8.87 (1H, dd, J 5 and 1.5), 8.33 (1H, s), 8.30 (1H, dd, J 8 and 1), 8.09 (1H, dd, J 7 and 2), 8.00-8.03 (1H, m), 7.94 (1H, dd, J 8 and 5), 7.72 (1H, dd, J 10 and 9), 7.54 (1H, d, J 7); m/z (ES+) 384.

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 4% methanol
  2. customcrystallisation from hot toluene

Sources & evidence

ORD record
ord-17f2046f85954181bab8d4d6f8b993d3
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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