Benzoyl chloride → HCID 86659859, compound

HRID 2360122Notes

Reaction equation

HRID 2360122 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2.C(N(CC)C(C)C)(C)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 107019745-methoxy-2,3-dihydro-1H-indole

Product 1

HCID 86659859HCID 86659859, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-methoxyindoline (202 mg, 1.35 mmol) and N,N-diisopropylethylamine (0.34 mL, 2.0 mmol) in 4.0 mL of dry dichloromethane was added benzoyl chloride (0.23 mL, 2.0 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 70/30) to obtain 5-methoxy-1-benzoylindoline (224 mg, 65%).

Workup

  1. washThe solution was washed with saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 70/30)

Sources & evidence

ORD record
ord-91e5c1a183de46128b4233682c74472b
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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