Potassium Carbonate → HCID 59026090, compound

HRID 639008Notes

Reaction equation

HRID 639008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:20][CH3:21])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CO[CH2:30][CH2:31]OC.O>>[CH:30]([C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[C:4]([O:20][CH3:21])[CH:5]=2)[N:10]=[CH:9][CH:8]=1)=[CH2:31]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 18180031Water 1,2-dimethoxyethaneHCID 85806400HCID 85806400, compound

Product 1

HCID 59026090HCID 59026090, compoundYield 65%

Conditions

Temperature
90 °C

Procedure

To a solution of 1,1,1-trifluoromethanesulfonic acid 8-fluoro-6-methoxy-quinolin-4-yl ester (1.0 g, 3.1 mmol), potassium carbonate (1.28 g, 9.3 mmole), tetrakis-triphenylphosphine (350 mg, 0.3 mmole) in DME/H2O (20 mL, 3:1) was added 2,4,6-trivinylcycloborane-pyridine complex (460 mg, 1.5 mmole). After stirring for 3 h at 90° C., the mixture contents were cooled to room temperature and extracted with diethyl ether. The ether fractions were combined, concentrated and purified by column chromatography (silica, 0-10% ethyl acetate in hexane) to give the title compound as a light yellow solid (428 mg, 65%): LC/MS (ES) m/e 212 (M+H)+.

Workup

  1. temperaturethe mixture contents were cooled to room temperature
  2. extractionextracted with diethyl ether
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica, 0-10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9697a265746842c086d41668fc40a40e
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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