Tetrabutylammonium Fluoride → 6-Benzenesulfonyl-5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole

HRID 1475328Notes

Reaction equation

HRID 1475328 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH3:30])([CH3:29])[CH2:15][N:16]3[Si](C(C)C)(C(C)C)C(C)C)=[CH:12][C:11]=2[F:31])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]1([S:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH3:29])([CH3:30])[CH2:15][NH:16]3)=[CH:12][C:11]=2[F:31])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867239486-Benzenesulfonyl-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole

Product 1

HCID 867239496-Benzenesulfonyl-5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indoleYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Benzenesulfonyl-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole (1.43 mg, 3.1 mmol) was treated with TBAF (1M solution in THF, 4.0 mL) in dry THF (20 mL) and the resulting solution stirred at room temperature for 1.5 hours. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The crude material was purified by chromatography (petrol:EtOAc 1:1) to give the title compound (810 mg) as a colourless oil. MS: [M+H]+=306.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. customThe crude material was purified by chromatography (petrol:EtOAc 1:1)

Sources & evidence

ORD record
ord-1141698ac3ba47e598118404418a4284
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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