Potassium Carbonate → HCID 89650960, compound

HRID 2174689Notes

Reaction equation

HRID 2174689 reaction equation
CC1S[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:25]([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH:13]1([C:14]2[N:6]=[C:5]([C:7]([O:9][CH3:25])=[O:8])[C:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:15]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 9435352-methyl-5-phenyl-1,3-thiazole-4-carboxylic Acid

Product 1

HCID 89650960HCID 89650960, compoundYield 74.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 6-Cyclopropyl-3-iodo-pyridine-2-carboxylic acid methyl ester (D85, 200 mg, 0.66 mmol), phenyl boronic acid (80.5 mg, 0.66 mmol) and Pd tetrakistriphenylphospine (76.3 mg; 0.066 mmol) in dry Toluene (3 ml) was added K2CO3 (1M acq solution, 0.66 ml, 0.66 mmol). The mixture was heated in microwave oven for 25 min at 120° C. The reaction mixture was diluted with AcOEt (10 mL) and water (10 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and filtrated. The solvent was evaporated under reduced pressure; the crude mixture was purified on silica gel (Cyclohexane to Cyclohexane/AcOEt 9:1) to obtain 125 mg of the title compound as white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. customthe crude mixture was purified on silica gel (Cyclohexane to Cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record
ord-2ee247eac92e41d4842ace4bf2569b27
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

Loading…