Potassium Carbonate → (S)-N-(5-((2-(trifluoromethyl)phenoxy)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 473110Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:17])([F:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].Cl[CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][C@H:24]([NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH2:23]2>CN(C=O)C>[F:7][C:8]([F:16])([F:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][C@H:24]([NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH2:23]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of potassium carbonate (0.174 mmol, 24.01 mg), 2-(trifluoromethyl)phenol (0.087 mmol, 14.08 mg), and (S)-N-(5-(chloromethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.087 mmol, 25 mg) in DMF (2 mL) was heated at 120° C. for 900 s in a Smith Synthesiser microwave. The reaction mixture was concentrated to dryness before DCM (2 mL) and H2O (2 mL) was added and the reaction mixture filtered through a hydrophobic frit washing with further DCM (2 mL). The DCM layer was concentrated to dryness and purified by preparative HPLC to furnish the desired product (10.0 mg, 27.8%). MS (ESI): m/z [M−H]− 412.2

Workup

concentrationThe reaction mixture was concentrated to dryness before DCM (2 mL) and H2O (2 mL)
additionwas added
filtrationthe reaction mixture filtered through a hydrophobic frit
washwashing with further DCM (2 mL)
concentrationThe DCM layer was concentrated to dryness
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-5292ea96289149bfbd9b3cb14c3da606
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

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