N,N-Dimethylglycine → N-[(2S)-5-(phenyloxy)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 1922298Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu]I>[C:18]1([O:24][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A reaction mixture of N-[(2S)-5-bromo-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.31 mmol, Description 1), phenol (30 mg, 0.32 mmol), caesium carbonate (308 mg, 0.94 mmol), copper(I) iodide (66 mg, 0.35 mmol) and N,N-dimethylglycine (39 mg, 0.38 mmol) in DMSO (1.5 ml) was heated in a microwave at 190° C. for 30 minutes. The mixture was quenched with hydrochloric acid (2M) and then partitioned between dichloromethane and water. The organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product. The crude product was purified using MDAP to obtain the title product as a yellow gum (49 mg).

Workup

customThe mixture was quenched with hydrochloric acid (2M)
custompartitioned between dichloromethane and water
dry with materialThe organic solution was dried (MgSO4)
customevaporated under reduced pressure
customto yield the crude product
customThe crude product was purified

Sources & evidence

ORD record: ord-5bbaad5538814ac695f1fc6d45a61833
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173820B2

Reaction notes

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