Potassium bis(trimethylsilyl)amide → HCID 86723956, compound

HRID 1475338Notes

Reaction equation

HRID 1475338 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH3:21])([CH3:20])[CH2:13][N:14]2[C:17](=[O:19])[CH3:18])=[CH:10][C:9]=1[F:22])(=[O:7])=[O:6].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:4]1([S:5]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([CH3:21])([CH3:20])[CH2:13][N:14]3[C:17](=[O:19])[CH3:18])=[CH:10][C:9]=2[F:22])(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 86723955HCID 86723955, compound

Product 1

HCID 86723956HCID 86723956, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[6-(3-chloro-propane-1-sulfonyl)-5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl]-ethanone (502 mg, 1.44 mmol) at −78° C. in THF (30 mL) under N2, KHMDS (0.5 M in toluene, 3 mL) was slowly added. The solution was stirred for 10 minutes at the same temperature and then 30 minutes at ambient temperature then quenched with 1 M hydrochloric acid and extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated. The crude material was purified by SiO2 chromatography (EtOAc:Petrol 1:1) to give the title compound (310 mg). MS: [M+H]+=312.

Workup

  1. custom30 minutes at ambient temperature then quenched with 1 M hydrochloric acid
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by SiO2 chromatography (EtOAc:Petrol 1:1)

Sources & evidence

ORD record
ord-312551363a124b058d947943c5d65eb0
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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