2H-pyran-3,5(4H,6H)-dione → methyl 2-ethyl-4-(4-fluoro-3-iodophenyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridin-3-carboxylate

HRID 987389Notes

Reaction equation

[NH2:1][C:2]([CH2:8][CH3:9])=[CH:3][C:4]([O:6][CH3:7])=[O:5].[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=1[I:19].[O:20]1[CH2:25][C:24](=O)[CH2:23][C:22](=[O:27])[CH2:21]1>C(O)C>[CH2:8]([C:2]1[NH:1][C:24]2[CH2:25][O:20][CH2:21][C:22](=[O:27])[C:23]=2[CH:15]([C:14]2[CH:17]=[CH:18][C:11]([F:10])=[C:12]([I:19])[CH:13]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

The product from Example 11A (1.4 g, 11 mmol), the product from Example 2C (2.9 g, 11 mmol) and the product from Example 1C (1.0 g, 8.8 mmol) were taken up in ethanol (15 mL), heated at 80° C. for 24 hours, stirred at ambient temperature for 36 hours and concentrated. The residue was purified by chromatography on silica gel eluting with 2% methanol in dichloromethane to provide the title compound.

Workup

concentrationconcentrated
customThe residue was purified by chromatography on silica gel eluting with 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-7fd4d66b75c749cc984ba1917b51755d
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632418B2

Reaction notes

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