Ethanol → Ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-imidazo[4,5-c]pyridin-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968083Notes

Reaction equation

HRID 1968083 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH:11]=O.[F:13][C:14]1[CH:31]=[CH:30][C:17](/[CH:18]=[N:19]/[C:20]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=2[CH2:22][O:23][C:24]3=[O:29])=[CH:16][CH:15]=1.[CH2:32]([OH:34])[CH3:33]>C(OCC)(=O)CC>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH:18]2[CH:11]([C:3]3[N:2]([CH3:1])[C:10]4[CH:9]=[CH:8][N:7]=[CH:6][C:5]=4[N:4]=3)[C:32](=[O:34])[C:33]3[C:25]([C:24]([O:23][CH2:22][CH3:21])=[O:29])=[CH:26][CH:27]=[CH:28][C:20]=3[NH:19]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 122393311-Methyl-1H-imidazo(4,5-c)pyridine-2-carboxaldehydeHCID 178519076HCID 178519076, compound

Product 1

HCID 67261937Ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-imidazo[4,5-c]pyridin-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Procedure

To a solution of 1-methyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde (400 mg, 2.48 mmol), (E)-4-(4-fluorobenzylideneamino) isobenzofuran-1(3H)-one (634 mg, 2.48 mmol) in ethyl propionate (20 ml) were added a solution of sodium ethanoxide in ethanol [sodium (171 mg, 7.45 mmol) in ethanol (10 mL)] at 0° C. Then the mixture was stirred at room temperature overnight. Then the mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product, which was purified by chromatography (silica gel, petroleum ether/ethyl acetate=25:1 to 5:1) to give the title compound (150 mg, yield 14%). LC-MS (ESI) m/z: 445 (M+1)+.

Workup

  1. customThen the mixture was quenched with water (10 mL) and solvent
  2. customwas removed in vacuum
  3. extractionThe residue was extracted with ethyl acetate (100 mL×4)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customwas purified by chromatography (silica gel, petroleum ether/ethyl acetate=25:1 to 5:1)

Sources & evidence

ORD record
ord-651b21b6d31847f7b537840c03bc16a0
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

Loading…