Potassium Carbonate → HCID 90409212, compound

HRID 516582Notes

Reaction equation

HRID 516582 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:13]([F:14])=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][Si](C)(C)C)=[CH:17][CH:16]=2)[N:11]=[C:10]([C:27]([O:29][CH3:30])=[O:28])[C:9]=1[Cl:31]>CO.O>[NH2:7][C:8]1[C:13]([F:14])=[C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[CH:22])=[CH:19][CH:20]=2)[N:11]=[C:10]([C:27]([O:29][CH3:30])=[O:28])[C:9]=1[Cl:31]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 90408305HCID 90408305, compound

Product 1

HCID 90409212HCID 90409212, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Potassium carbonate (100 mg, 0.74 mmol, 1.0 equiv) was added to a stirred mixture of methyl 4-amino-3-chloro-5-fluoro-6-(4-((trimethylsilyl)ethynyl)phenyl)picolinate (280 mg, 0.74 mmol, 0.10 equiv) in methanol (3.7 mL) at 23° C. The heterogeneous pale yellow mixture was stirred at 23° C. for 30 m. The reaction mixture was diluted with water (200 mL) and extracted with dichloromethane (5×50 mL). The organic layers were dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation to afford the title compound as a tan powder (220 mg, 96%).

Workup

  1. extractionextracted with dichloromethane (5×50 mL)
  2. dry with materialThe organic layers were dried (magnesium sulfate), gravity
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b3962d2ff9d14988a1b84f9cfc75544b
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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