Water → HCID 86616735, compound

HRID 735352Notes

Reaction equation

HRID 735352 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([S:27]([O-:29])=[O:28])[CH:21]=[CH:20]3)=[CH:13][CH:12]=1.[Na+].O>CS(C)=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([S:27]([C:2]2[N:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:29])=[O:28])[CH:21]=[CH:20]3)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7376072-Chloro-3-pyridinecarboxaldehydeHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 86616735HCID 86616735, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-chloronicotinaldehyde (228 mg, 1.62 mmol) and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (500 mg, 1.62 mmol) in DMSO (2.5 mL) was heated for 12 hours at 80° C. The reaction was poured into water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 35-60% ethyl acetate/isohexane, to give the title compound as solid (349 mg). 1H NMR (400 MHz, d6-DMSO): δ 11.00 (1H, s), 8.84-8.82 (2H, m), 8.40-8.34 (3H, m), 8.25 (1H, d, J=8.7 Hz), 8.06-8.02 (2H, m), 7.94-7.84 (3H, m), 7.38 (2H, t, J=8.8 Hz).

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 35-60% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-a16375cdcc8c47d5b008962ffefa0dfb
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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