Potassium Carbonate → HCID 90408754, compound

HRID 516584Notes

Reaction equation

HRID 516584 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[C:11]([F:17])[CH:10]=2)[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22].[C:23](=O)([O-])[O-].[K+].[K+].COP(C(=[N+]=[N-])C(=O)C)(=O)OC>CO>[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[CH:23])=[C:11]([F:17])[CH:10]=2)[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 90408741HCID 90408741, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 90408754HCID 90408754, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-amino-3-chloro-6-(3-fluoro-4-formylphenyl)-5-methylpicolinate (358 mg, 1.1 mmol) and potassium carbonate (537 mg, 3.9 mmol) in methanol (11 mL) at room temperature was added 1 mL of dimethyl(1-diazo-2-oxopropyl)phosphonate (Bestmann-Ohira reagent, crude reagent) for 3 h. The reaction was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic layers were dried organics over anhydrous sodium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-50% ethyl acetate/hexanes) provided the title compound as a yellow solid (245 mg, 69%).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×)
  3. filtrationfiltered
  4. customPurification by flash chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b4522bdda439464cab12d8c9dbf1e94b
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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