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

HRID 1922301Notes

Reaction equation

HRID 1922301 reaction equation
[OH:1][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.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu]I>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:1][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

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 44124720N-[(2S)-5-(2-pyridinyloxy)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideYield 32.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
190 °C

Procedure

A reaction mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.39 mmol, Description 3), 2-bromopyridine (62 mg, 0.39 mmol), caesium carbonate (382 mg, 1.17 mmol), copper(I) iodide (82 mg, 0.43 mmol) and N,N-dimethylglycine (49 mg, 0.47 mmol) in DMSO (1.5 ml) was heated in a microwave at 190° C. for 30 minutes. The resulting mixture was then partitioned between dichloromethane and water and the organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product. The crude product was purified using MDAP. The resulting solution was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure to obtain the title compound as a yellow gum (42 mg).

Workup

  1. customThe resulting mixture was then partitioned between dichloromethane and water
  2. dry with materialthe organic solution was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto yield the crude product
  5. customThe crude product was purified
  6. additionThe resulting solution was diluted with saturated aqueous sodium bicarbonate solution
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic solution was dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b3067db738094521aab945ce0fb4d209
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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