Water → HCID 80640449, compound

HRID 2054155Notes

Reaction equation

HRID 2054155 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[C:11]1[N:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1.O>CN(C=O)C.CCOC(C)=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[S:1][C:11]1[N:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 178418616HCID 178418616, compound

Product 1

HCID 80640449HCID 80640449, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-mercaptopyridine (6.39 g, 57.4 mmol) in DMF (100 mL) was added NaH (60% dispersion in oil, 2.29 g, 57.2 mmol) in portions and the mixture was stirred for 15 min. 6-Bromo-3-pyridine carboxaldehyde (9.28 g, 49.9 mmol) was added and the resultant mixture was stirred for 1 h. Water was added followed by the addition of EtOAc. The phases were separated and the aqueous layer was extracted with EtOAc (2×). The organic extracts were combined, dried over Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by flash column chromatography (eluents: 20% EtOAc in hexanes and 30% EtOAc in hexanes). Evaporation of the appropriate fractions gave a white solid, which was further purified by recrystallization from diethyl ether to give the product as a white solid (9.66 g, 90% yield). 1H NMR (CDCl3) δ 10.00 (s, 1H), 8.89-8.84 (m, 1H), 8.67-8.64 (m, 1H), 8.01 (dd, J=2.2, 8.9 Hz, 1H), 7.76 (dt, J=2.2, 8.3 Hz, 1H), 7.67-7.63 (m, 1H), 7.44 (d, J=8.3 Hz, 1H), 7.35-7.29 (m, 1H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas purified by flash column chromatography (eluents: 20% EtOAc in hexanes and 30% EtOAc in hexanes)
  8. customEvaporation of the appropriate fractions
  9. customgave a white solid, which
  10. customwas further purified by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-324535b13f3a4643b1e3fd06f0ff148c
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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