Potassium Carbonate → HCID 67974069, compound

HRID 2168222Notes

Reaction equation

HRID 2168222 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1([F:28])[CH2:27][CH2:26][NH:25][CH2:24]1>C(#N)C>[F:22][C:23]1([F:28])[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27828273,3-DifluoropyrrolidineHCID 54408639Ethyl 3-(2-bromoethoxy)benzoate

Product 1

HCID 67974069HCID 67974069, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of ethyl 3-[(2-bromoethyl)oxy]benzoate D46 (476 mg) and potassium carbonate (481 mg, 3.48 mmol) in Acetonitrile (20 mL) stirred at 20° C. was added 3,3-difluoropyrrolidine (250 mg, 1.741 mmol). The reaction mixture was stirred at 70° C. for 36 h. After cooled to room temperature the mixture was filtrated and the filtrate was concentrated. The crude product was added to a silica gel column and was eluted with Hexane/EtOAc/TEA in ratio 50/50/0.5. Fractions isolated and solvent evaporated to afford the title product D49 in 400 mg as a yellow oil. LCMS Retention time=1.20 mins, [M+H]+300 (5 min run)

Workup

  1. temperatureAfter cooled to room temperature the mixture
  2. filtrationwas filtrated
  3. concentrationthe filtrate was concentrated
  4. additionThe crude product was added to a silica gel column
  5. washwas eluted with Hexane/EtOAc/TEA in ratio 50/50/0.5
  6. customFractions isolated
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-161b97ea9af843c6b3d2667c04ddc91d
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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