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

HRID 1603760Notes

Reaction equation

HRID 1603760 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 mmol), 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-09d7b52d8f7247fc811a5a08d54bdd64
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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