Ethyl Acetate → HCID 67260487, compound

HRID 1968164Notes

Reaction equation

HRID 1968164 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[F:9][C:10]1[CH:15]=[CH:14][C:13](/[C:16](=[N:18]/[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][O:22][C:23]3=[O:28])/[CH3:17])=[CH:12][CH:11]=1.[CH3:29][CH2:30][O-:31].[Na+].C(OCC)(=O)C>C(OCC)(=O)CC>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([CH3:17])[CH:7]([C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=3)[C:30](=[O:31])[C:29]3[C:24]([C:23]([O:22][CH2:21][CH3:20])=[O:28])=[CH:25][CH:26]=[CH:27][C:19]=3[NH:18]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2723922Sodium ethoxideHCID 178463257HCID 178463257, compound

Product 1

HCID 67260487HCID 67260487, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 1-methyl-1H-imidazole-2-carbaldehyde (580 mg, 5.2 mmol), and (E)-4-(1-(4-fluorophenyl)ethylideneamino)isobenzofuran-1(3H)-one (1 g, 3.7 mmol) in ethyl propionate (20 ml) was added rapidly EtONa [sodium (340 mg, 14.8 mmol) in 8 mL ethanol] at 0° C., then the mixture was stirred at 30° C. for 3 hr. The resulting mixture was added ethyl acetate (150 mL) and washed with water (25 mL×3), the organic layers were combined and evaporated to dryness to give the crude product, which was purified by column chromatography (silica gel, dichloromethane:methanol=200:1 to 50:1) to afford the title compound as a red solid (120 mg, yield 8%). LC-MS (ESI) m/z: 408 (M+1)+

Workup

  1. washwashed with water (25 mL×3)
  2. customevaporated to dryness
  3. customto give the crude product, which
  4. customwas purified by column chromatography (silica gel, dichloromethane:methanol=200:1 to 50:1)

Sources & evidence

ORD record
ord-8d4b32376f5b4546b738e0bceb6e2ab8
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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