Ethanol → HCID 67260753, compound

HRID 908013Notes

Reaction equation

HRID 908013 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[F:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][O:16][C:17]2=[O:20])=[C:13](/[N:21]=[CH:22]/[C:23]2[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=2)[CH:12]=1.[O-:29][CH2:30][CH3:31].[Na+].C(O)C>C(OCC)(=O)CC>[F:10][C:11]1[CH:19]=[C:18]([C:17]([O:16][CH2:15][CH3:14])=[O:20])[C:31]2[C:30](=[O:29])[CH:6]([C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)[CH:22]([C:23]3[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)[NH:21][C:13]=2[CH:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxideHCID 178480587HCID 178480587, compound

Product 1

HCID 67260753HCID 67260753, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-fluorobenzaldehyde (248 mg, 2 mmol) and (E)-6-fluoro-4-((1-methyl-1H-imidazol-2-yl)methyleneamino)isobenzofuran-1(3H)-one (518 mg, 2 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (184 mg, 8 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 0.5 hr. The mixture was quenched with water (20 mL) and solvents were removed in vacuum. The residues were dissolved in water and extracted with ethyl acetate three times. The combined organic layers were washed with water and brine. After the removal of solvents, the crude product was purified by flash column chromatography to obtain a yellow solid, which was dried in vacuum at 50° C. to give the title compound (200 mg, yield: 24%). LC-MS (ESI) m/z: 412 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (20 mL) and solvents
  3. customwere removed in vacuum
  4. dissolutionThe residues were dissolved in water
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic layers were washed with water and brine
  7. customAfter the removal of solvents
  8. customthe crude product was purified by flash column chromatography
  9. customto obtain a yellow solid, which
  10. customwas dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-bd52c3ad192f4b318e80ee28ee09f414
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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