Potassium Carbonate → HCID 68276186, compound

HRID 1400312Notes

Reaction equation

HRID 1400312 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].C([O-])([O-])=O.[K+].[K+].Br[C:20]([F:31])([F:30])[C:21]([NH:23][CH2:24][C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)=[O:22]>CC(C)=O.C(OCC)(=O)C>[F:31][C:20]([F:30])([O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[F:1])[C:21]([NH:23][CH2:24][C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)=[O:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110949481-fluoronaphthalen-2-olHCID 68276609HCID 68276609, compound

Product 1

HCID 68276186HCID 68276186, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-fluoronaphthalen-2-ol (280 mg, 1.73 mmol) and K2CO3 (1.2 g, 8.65 mmol) in 10 mL of acetone, 2-bromo-2,2-difluoro-N-(furan-2-ylmethyl)acetamide (527 mg, 2.08 mmol) were added. The resulting mixture was stirred at 40° C. overnight. The reaction was cooled at room temperature, diluted with ethyl acetate (30 mL) and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 2,2-difluoro-2-[(1-fluoronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)acetamide as red oil (650 mg) which was used in the next step without further purification.

Workup

  1. temperatureThe reaction was cooled at room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60a245fc14e544ed9572728abf6cc3e1
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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