Potassium Carbonate → HCID 90409227, compound

HRID 516568Notes

Reaction equation

HRID 516568 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Si](C)(C)C)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23].C(=O)([O-])[O-].[K+].[K+].[Br:30]Br>ClCCCl>[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Br:30])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 90409195HCID 90409195, compound

Product 1

HCID 90409227HCID 90409227, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To methyl 4-amino-3-chloro-5-methyl-6-(4-(trimethylsilyl)phenyl)picolinate (150 mg, 0.43 mmol) and potassium carbonate (215 mg, 1.56 mmol) in 1,2-dichloroethane (DCE, 2.9 mL) was added bromine (0.03 mL, 0.58 mmol) and stirred at room temperature for 18 h. The DCE was concentrated off under vacuum and the crude material was partitioned between ethyl acetate and aqueous potassium carbonate. The aqueous layer was extracted with ethyl acetate (3×), washed with water, dried over anhydrous magnesium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-40% ethyl acetate/hexanes) afforded the title compound as a yellow solid (68 mg, 45%).

Workup

  1. concentrationThe DCE was concentrated off under vacuum
  2. customthe crude material was partitioned between ethyl acetate and aqueous potassium carbonate
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customPurification by flash chromatography (0-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cd0902f045c747b7a3b33052b3ba8379
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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