Sodium ethoxide → Ethyl 7-fluoro-2-(4-fluorophenyl)-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907896Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[C:4](/[N:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:3]=1.[CH3:21][N:22]1[C:26]([CH:27]=O)=[N:25][CH:24]=[N:23]1.[CH3:29][CH2:30][O-:31].[Na+]>C(OCC)(=O)CC>[F:1][C:2]1[CH:10]=[C:9]([C:8]([O:7][CH2:6][CH3:5])=[O:11])[C:29]2[C:30](=[O:31])[CH:27]([C:26]3[N:22]([CH3:21])[N:23]=[CH:24][N:25]=3)[CH:13]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[NH:12][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (E)-6-fluoro-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (4 g, 14.6 mmol) and 1-methyl-1H-1,2,4-triazole-5-carbaldehyde (4.1 g, 36.9 mmol) in ethyl propionate (220 mL) was added EtONa ((sodium 940 mg, 40.9 mmol), in 70 mL ethanol) at 37° C., then the mixture was stirred at 40° C. for 6 hr. The resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4).The extract was concentrated to dryness to give a crude product, which was purified by column chromatography (silica gel, dichloromethane:methanol=200:1 to 100:1) to obtain a green solid (1.02 g, yield 14%). LC-MS (ESI) m/z: 413 (M+1)+.

Workup

customThe resulting mixture was evaporated under reduced pressure
extractionextracted with ethyl acetate (100 mL×4).The extract
concentrationwas concentrated to dryness
customto give a crude product, which
customwas purified by column chromatography (silica gel, dichloromethane:methanol=200:1 to 100:1)

Sources & evidence

ORD record: ord-ab99cb46dda545ff8c5cf98d3ee5b46f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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