Bromine → 5'-Bromo-7'-fluorospiro[cyclopropane-1,3'-indolin]-2'-one

HRID 2250525Notes

Reaction equation

HRID 2250525 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])[C:7]12[CH2:13][CH2:12]1.C([O-])(=O)C.[Na+].[Br:19]Br>C(Cl)Cl.CCOCC>[Br:19][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][C:8](=[O:11])[C:7]12[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 602091727'-Fluorospiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 602091735'-Bromo-7'-fluorospiro[cyclopropane-1,3'-indolin]-2'-oneYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

7′-Fluorospiro[cyclopropane-1,3′-indol]-2′(1′H)-one (0.54 g, 3.05 mmol) was dissolved in 20 mL of CH2Cl2 and sodium acetate (0.28 g, 3.36 mmol) was added followed by bromine (0.173 mL, 3.36 mmol). The mixture was stirred at 25° C. for 16 h then diluted with ether and washed with Na2S3O3, sodium bicarbonate, water, brine, dried over MgSO4, and concentrated. Purification by flash chromatography (15% acetone/hexane) afforded 5′-Bromo-7′-fluorospiro[cyclopropane-1,3′-indol]-2′(1′H)-one (0.64 g, 82%) as a white solid:

Workup

  1. washwashed with Na2S3O3, sodium bicarbonate, water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography (15% acetone/hexane)

Sources & evidence

ORD record
ord-c7efae6d294848b9bb0fc73ea2cec4dd
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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