2,6-Dibromopyridine → 3-(6-Bromopyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine

HRID 1796007Notes

Reaction equation

HRID 1796007 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:10]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[N:14][C:9]2=[N:8][CH:7]=1)CCC.[Br:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30](Br)[N:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:27][C:28]1[N:29]=[C:30]([C:6]2[N:10]3[CH:11]=[CH:12][C:13]([C:15]([F:16])([F:17])[F:18])=[N:14][C:9]3=[N:8][CH:7]=2)[CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 122742,6-DibromopyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 99280253-(6-Bromopyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To the degassed solution of 3-tributylstannyl-7-trifluoromethyl-imidazo[1,2-α]pyrimidine was added 2,6-dibromopyridine (1.8 g, 7.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (218 mg, 0.18 mmol) and the mixture heated at reflux for 3 h. The crude reaction was adsorbed onto silica and purified by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-60%) to give a yellow solid. Crystallisation from ethyl acetate/isohexane afforded 3-(6-bromopyridin-2-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (702 mg) as a white solid: δH (400 MHz, DMSO) 7.64 (1H, d, J 9), 7.83 (1H, d, J 8), 7.93 (1H, dd, J 9 and 9), 8.20 (1H, d, J 9), 8.92 (1H, s), 10.18 (1H, d, J 9); m/z (ES+) 343, 345 (M++H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. customThe crude reaction
  4. custompurified by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-60%)
  5. customto give a yellow solid
  6. customCrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-2207dec6b8134659b7f95f0b168010bc
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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