Benzenesulfonyl fluoride → 6-Benzenesulfonyl-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole

HRID 1475327Notes

Reaction equation

HRID 1475327 reaction equation
[Li]CCCC.Br[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:27])([CH3:26])[CH2:12][N:13]2[Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:9][C:8]=1[F:28].[C:29]1([S:35](F)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[C:29]1([S:35]([C:7]2[CH:15]=[C:14]3[C:10]([C:11]([CH3:27])([CH3:26])[CH2:12][N:13]3[Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:9][C:8]=2[F:28])(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 67779Benzenesulfonyl fluorideHCID 867239466-Bromo-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 867239486-Benzenesulfonyl-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indoleYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

BuLi (2.2 M solution in Et2O. 2.4 mL, 5.4 mmol) was slowly added to a solution of 6-bromo-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole (1.8 g, 4.5 mmol) in THF (20 mL) at −78° C. under nitrogen. The solution was stirred for 15 minutes at −78° C. and then phenylsulfonyl fluoride (541 μL, 4.5 mmol) was slowly added. Stirring was maintained for 1 h at the same temperature. The reaction was quenched by adding saturated aqueous NH4Cl and the product was extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated. The crude material was purified by SiO2 chromatography (10% EtOAc in petrol) to give the title compound (1.4 g) as a yellow solid. 1H NMR (CDCl3): 7.98 (2H, d), 7.64-7.56 (1H, m), 7.56-7.48 (2H, m), 7.23 (1H, d), 6.68 (1H, d), 3.50 (2H, s), 1.55-1.45 (3H, m), 1.24 (6H, s), 1.21-1.11 (18H, m).

Workup

  1. stirringStirring
  2. temperaturewas maintained for 1 h at the same temperature
  3. customThe reaction was quenched
  4. additionby adding saturated aqueous NH4Cl
  5. extractionthe product was extracted with EtOAc
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by SiO2 chromatography (10% EtOAc in petrol)

Sources & evidence

ORD record
ord-2ecf96df245d41b5996cdab8cd42c11d
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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