1,1-Dibromoethane → 7'-Fluorospiro[cyclopropane-1,3'-indolin]-2'-one

HRID 2250524Notes

Reaction equation

HRID 2250524 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.[Cl-].[Li+].[CH2:14]([Li])[CH2:15]CC.BrC(Br)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]12[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 112011,1-DibromoethaneHCID 433294Lithium ChlorideHCID 37343717-Fluoro-2,3-dihydro-1h-indol-2-oneHCID 178418339Butyllithium

Product 1

HCID 602091727'-Fluorospiro[cyclopropane-1,3'-indolin]-2'-oneYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

7-Fluorooxindole (1.28 g, 8.50 mmol) and lithium chloride (0.899 g, 21.3 mmol) were suspended in 80 mL of THF and cooled to 0° C. n-Butyllithium (8.5 mL, 16.9 mmol) was added slowly, and the mixture was stirred for 20 min, and then dibromoethane (0.73 mL, 8.5 mmol) was added. The mixture was warmed to 25° C. and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl and diluted with ether. The organics were washed with water, brine, dried over MgSO4, and concentrated. Flash chromatography (10% acetone/hexane) afforded 0.54 g (36%) of 7′-fluorospiro[cyclopropane-1,3′-indol]-2′(1′H)-one as a white solid: HRMS: calcd for C10H8FNO, 177.0590; found (ESI, [M+H]+), 178.0659

Workup

  1. additionwas added slowly
  2. stirringstirred for 16 h
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. additiondiluted with ether
  5. washThe organics were washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0dd41841ff43499b9dec52a9cb91a9d1
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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