Ammonium Chloride → 1-(6-Ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

HRID 1475321Notes

Reaction equation

HRID 1475321 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[N:7]([C:16](=[O:18])[CH3:17])[CH2:6][C:5]2([CH3:20])[CH3:19].[NH4+].[Cl-]>C1COCC1.[Zn]>[CH2:14]([S:11]([C:10]1[CH:9]=[C:8]2[C:4]([C:5]([CH3:19])([CH3:20])[CH2:6][N:7]2[C:16](=[O:18])[CH3:17])=[CH:3][CH:2]=1)(=[O:12])=[O:13])[CH3:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 709799561-(5-Bromo-6-ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

Product 1

HCID 709808661-(6-Ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanoneYield 92.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-bromo-6-ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (180 mg, 0.5 mmol) in THF (5 mL) containing saturated aqueous NH4Cl (1 mL), zinc dust (325 mg, 5 mmol) was added. The suspension was stirred at room temperature for 3 days and then partitioned between water and EtOAc. The aqueous phase was extracted twice with EtOAc. The organic extracts were filtered through a plug of Celite and the filtrate was evaporated in vacuo to give the title compound (130 mg) as a colourless gum which was used in the next step without further purification. MS: [M+H]+=282.

Workup

  1. additionwas added
  2. custompartitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted twice with EtOAc
  4. filtrationThe organic extracts were filtered through a plug of Celite
  5. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-eae7b1428e5f4013a3dc80ec682482f3
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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