Potassium Carbonate → HCID 70223134, compound

HRID 473093Notes

Reaction equation

HRID 473093 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:7][CH2:6]2.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:19][C:20]([F:28])([F:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679582-TrifluoromethylphenolHCID 67088048N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

Product 1

HCID 70223134HCID 70223134, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (30 mg, 0.104 mmol), 2-(trifluoromethyl)phenol (16.90 mg, 0.104 mmol), and potassium carbonate (28.8 mg, 0.208 mmol) in N,N-dimethylformamide (1 mL) was stirred at 60° C. overnight. The reaction mixture was partitioned between aq. sat. NaHCO3 (4 mL) and DCM (4 mL), filtered over a phase separator, and the organic phase was concentrated by blow down. Purification by flash chromatography (0-60% EtOAc in Heptane) and freeze drying from acetonitrile/water gave the title compound as a white solid (24 mg, 55.7%). MS (ESI): m/z [M−H]− 412.0.

Workup

  1. customThe reaction mixture was partitioned between aq. sat. NaHCO3 (4 mL) and DCM (4 mL)
  2. filtrationfiltered over a phase separator
  3. concentrationthe organic phase was concentrated by blow down
  4. customPurification by flash chromatography (0-60% EtOAc in Heptane)
  5. dry with materialfreeze drying from acetonitrile/water

Sources & evidence

ORD record
ord-5cf9f1dcdc244381ba3ec5eee16aba13
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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