Methanol → HCID 10172313, compound

HRID 916927Notes

Reaction equation

HRID 916927 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]([C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[CH3:24][OH:25].[CH3:26][Si]([CH:30]=[N+:31]=[N-])(C)C>C(Cl)Cl>[CH3:24][O:25][C:12]1[C:11]([C:30]#[N:31])=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:13]=1.[CH3:24][O:25][C:12]1[C:11]([C:15]([O:17][CH3:26])=[O:16])=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 69415322HCID 69415322, compound

Product 2

HCID 10172313HCID 10172313, compoundHCID 10236695HCID 10236695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (50 mg, 0.15 mmol) from Example 1, Step C (containing a trace of the 3-nitrile starting material) in methylene chloride (3 mL) and methanol (1 mL) was added 2M trimethylsilyldiazomethane in hexanes until the yellow color persisted. The volatiles were removed under a stream of nitrogen and the residue was separated by preparative TLC on silica gel (eluted with 30% ethyl acetate in hexanes) to obtain 2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-nitrile (A) and methyl 2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-carboxylate (B) as minor products (along with some of the N-alkylation by-products). The main product was the expected methyl 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (same product as obtained in Example 1, Step D).

Workup

  1. customThe volatiles were removed under a stream of nitrogen
  2. customthe residue was separated by preparative TLC on silica gel (eluted with 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-82656884d5bc45698747ccf89ec189d6
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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