Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 10133066, compound

HRID 2183954Notes

Reaction equation

HRID 2183954 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:14])=[C:6]([C:8]2[N:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:20]1[N:24]2[CH:25]=[CH:26][C:27]([C:29]([F:32])([F:31])[F:30])=[N:28][C:23]2=[N:22][CH:21]=1)CCC>>[F:14][C:5]1[CH:4]=[CH:3][C:2]([C:20]2[N:24]3[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[N:28][C:23]3=[N:22][CH:21]=2)=[CH:7][C:6]=1[C:8]1[N:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22329531HCID 22329531, compound

Product 1

HCID 10133066HCID 10133066, compound

Procedure

3-(5-Bromo-2-fluorophenyl)pyridazine (80.6 mg, 0.3 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.45 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-(pyridazin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 9.24 (1H, dd, J 5 and 1), 8.92 (1H, d, J 7), 8.48 (1H, dd, J 7 and 2), 8.16 (1H, s), 8.07-8.11 (1H, m), 7.66-7.71 (1H, m), 7.63 (1H, dd, J 9 and 5), 7.45 (1H, dd, J 11 and 9), 7.30 (1H, d, J 7); m/z (ES+) 359 (M++H).

Workup

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

Sources & evidence

ORD record
ord-3d2c0d8df626443d838a5a70da414a53
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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