5-Bromo-2-fluoropyridine → HCID 9835438, compound

HRID 1796047Notes

Reaction equation

HRID 1796047 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[C:28]1[CH:29]=[CH:30][C:31]([F:34])=[N:32][CH:33]=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>[F:34][C:31]1[CH:30]=[CH:29][C:28]([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:33][N:32]=1

Participants

4

Reactant 2

HCID 27831685-Bromo-2-fluoropyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9835438HCID 9835438, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a degassed solution of 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine was added 5-bromo-2-fluoropyridine (0.128 ml, 1.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (173 mg, 0.15 mmol) and the mixture heated at reflux for 5 h. The crude reaction was washed with water and extracted with ethyl acetate. After adding isohexane a dark solid was collected by suction filtration. The solid was adsorbed onto silica and purified by chromatography on silica gel, eluting with isohexane on a gradient of ethyl acetate (20-60%), to give 3-(2-fluoropyridin-5-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (150 mg) as a dark solid: δH (500 MHz, CDCl3) 7.12 (1H, m), 7.30 (1H, d, J 7), 7.99-8.02 (1H, m), 8.10 (1H, s), 8.46 (1H, s), 8.72 (1H, d, J 7); m/z (ES+) 282, 283 (M++H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 h
  3. customThe crude reaction
  4. washwas washed with water
  5. extractionextracted with ethyl acetate
  6. additionAfter adding isohexane a dark solid
  7. filtrationwas collected by suction filtration
  8. custompurified by chromatography on silica gel
  9. washeluting with isohexane on a gradient of ethyl acetate (20-60%)

Sources & evidence

ORD record
ord-8614ba75b14f41fb9e17003490058d4b
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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