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

HRID 1977732Notes

Reaction equation

HRID 1977732 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-bc8f6ed02976428cadbbb5818506f51f
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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