Ethyl 5-bromopyridine-3-carboxylate → HCID 18005196, compound

HRID 989172Notes

Reaction equation

HRID 989172 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[Sn](CCCC)(CCCC)CCCC.Br[C:23]1[CH:24]=[N:25][CH:26]=[C:27]([CH:33]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1(C)C(C)=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:23]1[CH:24]=[N:25][CH:26]=[C:27]([CH:33]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 2

HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 18005066HCID 18005066, compound

Product 1

HCID 18005196HCID 18005196, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of (2,6-difluorophenyl)tributyltin (1.18 g, 2.9 mol), ethyl 5-bromonicotinate (0.69 g, 3 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.10 g) in xylene (10 mL) was heated under reflux for 24 h, then cooled, filtered and evaporated. The residue was chromatographed on silica gel eluted with 20% ethyl acetate/petrol to give the title compound (0.64 g, 84%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 20% ethyl acetate/petrol

Sources & evidence

ORD record
ord-bcc7cb4b096c42e9b8d14927df1ea757
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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