Methanol → Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridine-3-carboxylate

HRID 8813

Reaction equation

HRID 8813 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:16]([CH:17]=[O:18])[C:11]2=[CH:10][C:9]=1[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.[C-]#N.[Na+].[CH3:35][OH:36]>[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:16]([C:17]([O:36][CH3:35])=[O:18])[C:11]2=[CH:10][C:9]=1[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 100953686-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 10005452Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

A 10 mL rb flask equipped with a magnetic stir bar and a septum was charged with a solution of 50 mg (0.11 mmol) of the product of Example 90, in 2 mL MeOH, 24 mg (0.27 mmol) of manganese dioxide and ca. 5 mg of sodium cyanide was added. The reaction mixture was stirred at room temperature for 4 h, then filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 0–10% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 482.2 (M+1), 484.0 (M+3); Rt=4.57 min.

Workup

  1. customA 10 mL rb flask equipped with a magnetic stir bar
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was purified on a silica gel flash chromatography column
  5. washeluted with 0–10% EtOAc-hexane
  6. customEvaporation of the purified fractions
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-8d62e65ff015489fb58702512914ae73
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Linked notes

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