3-Bromo-4-fluorobenzaldehyde → methyl 4-(3-bromo-4-fluorophenyl)-2,6-dimethyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

HRID 478305Notes

Reaction equation

HRID 478305 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH2:6][C:5](=O)[CH2:4][O:3]1.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=O.[NH2:20]/[C:21](/[CH3:27])=[CH:22]\[C:23]([O:25][CH3:26])=[O:24]>C(O)C>[Br:10][C:11]1[CH:12]=[C:13]([CH:14]2[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:27])[NH:20][C:5]3[CH2:4][O:3][CH:2]([CH3:1])[C:7](=[O:8])[C:6]2=3)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 234974742-methyl-2H-pyran-3,5(4H,6H)-dione

Product 1

HCID 18000971methyl 4-(3-bromo-4-fluorophenyl)-2,6-dimethyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 84C (1.3 g, 10 mmol), 3-bromo-4-fluorobenzaldehyde (2.4 g, 12 mmol) and methyl 3-aminocrotonate (1.2 g, 10 mmol) in ethanol (10 mL) were heated at 80° C. in a sealed tube for 60 hours. After cooling to ambient temperature, the mixture was filtered and the filtercake washed with ethanol and dried to provide the title compound. The filtrate was concentrated and chromatographed on silica gel eluting with 1% and then 2% and then 5% methanol in dichloromethane to provide additional quantities of the title compound.

Workup

  1. filtrationthe mixture was filtered
  2. washthe filtercake washed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-e24da46e56ea44a691c6fd45d4528e1a
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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