Ammonium Chloride → 6-Bromospiro[indoline-3,3'-thietan]-2-one

HRID 1618783Notes

Reaction equation

HRID 1618783 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:25]OS(C)(=O)=O)([CH2:19]OS(C)(=O)=O)[C:7](=[O:18])[N:8]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.O.O.O.O.O.O.O.O.O.[S-2:40].[Na+].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:18])[C:6]3([CH2:19][S:40][CH2:25]3)[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 73972Sodium sulfide nonahydrateHCID 58221521Tert-butyl 6-bromo-3,3-bis((methylsulfonyloxy)methyl)-2-oxoindoline-1-carboxylate

Product 1

HCID 670953256-Bromospiro[indoline-3,3'-thietan]-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of tert-butyl 6-bromo-3,3-bis((methylsulfonyloxy)methyl)-2-oxoindoline-1-carboxylate (3.70 g, 7.0 mmol) in anhydrous DMF (33 mL, deoxygenated with argon for 10 min) was added sodium sulfide nonahydrate (1.01 g, 4.20 mmol) under an argon atmosphere. The solution was stirred at 110° C. for 3 h, poured into saturated aqueous ammonium chloride solution and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. Purification by column chromatography (eluting with a gradient of 10-50% EtOAc in hexanes) gave 6-bromospiro[indoline-3,3′-thietan]-2-one as a yellow solid. Mass Spectrum (ESI) m/e=270.0 [(M+1) (79Br)] and 271.9 [(M+1) (81Br)].

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by column chromatography (
  6. washeluting with a gradient of 10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1cab3996f21a4abe936a1876ade8e30a
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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