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

HRID 473092Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([F:35])([F:34])[F:33]>CN(C)C=O>[F:33][C:32]([F:34])([F:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

N-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (50 mg, 0.196 mmol) was dissolved in N,N-dimethylformamide (dry) (2 mL), potassium carbonate (54.1 mg, 0.392 mmol) and 1-(bromomethyl)-2-(trifluoromethyl)benzene (94 mg, 0.392 mmol) were added and the mixture was stirred at 60° C. for 3 hr. After this time, the reaction mixture was partitioned between EtOAc and H2O, the organic layer separated and solvent evaporated in vacuo. Purification by flash chromatography (0-100% EtOAc in heptane) afforded the title compound as a colourless oil (34 mg, 42%). MS (ESI): m/z [M−H]− 412.0

Workup

customAfter this time, the reaction mixture was partitioned between EtOAc and H2O
customthe organic layer separated
customsolvent evaporated in vacuo
customPurification by flash chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record: ord-3bf2bf8cd3dc4254879c786472acc3a2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

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