Potassium Carbonate → HCID 90408843, compound

HRID 516583Notes

Reaction equation

[N+](=[C:3](P(=O)(OC)OC)C(=O)C)=[N-].[NH2:13][C:14]1[C:19]([F:20])=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]=O)=[C:23]([F:29])[CH:22]=2)[N:17]=[C:16]([C:30]([O:32][CH3:33])=[O:31])[C:15]=1[Cl:34].C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:13][C:14]1[C:19]([F:20])=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[CH:3])=[C:23]([F:29])[CH:22]=2)[N:17]=[C:16]([C:30]([O:32][CH3:33])=[O:31])[C:15]=1[Cl:34]

Participants

Conditions

Temperature: 23 °C

Procedure

Dimethyl 1-diazo-2-oxopropylphosphonate (290 mg, 1.5 mmol, 1.2 equiv) was added to a stirred mixture of methyl 4-amino-3-chloro-5-fluoro-6-(3-fluoro-4-formylphenyl)picolinate (410 mg, 1.3 mmol, 1.0 equiv) and solid potassium carbonate (350 mg, 2.5 mmol, 2.0 equiv) in methanol (12 mL) at 23° C. The resulting cloudy pale yellow mixture was stirred at 23° C. for 2 h. The reaction mixture was diluted with water (150 mL) and extracted with dichloromethane (4×60 mL). The organic layers were dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (33% ethyl acetate in hexanes) to afford the title compound as a white powder (150 mg, 38%).

Workup

extractionextracted with dichloromethane (4×60 mL)
dry with materialThe organic layers were dried (magnesium sulfate), gravity
filtrationfiltered
concentrationconcentrated by rotary evaporation
customThe residue was purified by silica gel column chromatography (33% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-fa4cbc4e205240ac8de27a71d1c2e4d6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09113629B2

Reaction notes

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