Ethyl Acetate → Bpr-0L075

HRID 490781Notes

Reaction equation

HRID 490781 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18].C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-].CCOC(C)=O>C(Cl)Cl.CC[Mg+].[Br-].[Cl-].[Cl-].[Zn+2].CCCCCC>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:17]([C:16]3[CH:20]=[C:21]([O:25][CH3:26])[C:22]([O:23][CH3:24])=[C:14]([O:13][CH3:12])[CH:15]=3)=[O:18])=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 766596-Methoxy-1H-indoleHCID 6451240Aluminum(III) ChlorideHCID 865899753,4,5-trimethoxybenzoyl chloride CH2Cl2

Product 1

HCID 10359957Bpr-0L075Yield 72%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 178461630HCID 178461630, compoundSolvent

Procedure

To a mixture of 6-methoxyindole (0.3 g, 2.03 mmol) and anhydrous ZnCl2 (0.56 g, 4.07 mmol) in CH2Cl2 (10 mL), EtMgBr (0.9 ml, 3 M) was added over 10 min at room temperature. The obtained suspension was stirred for 1 hr. To the suspension, the solution of 3,4,5-trimethoxybenzoyl chloride/CH2Cl2 (10 ml) was added dropwisely during 5 min for a coupling reaction. The reaction mixture continued stirring for another 1 hr and AlCl3 (0.27 g, 2.03 mmol) was added. The resultant thick mixture was vigorously stirred for 5 hr while monitoring by TLC (EtOAc: n-hexane=1:1). The reaction was quenched with H2O (10 ml) and extracted with CH2Cl2 (10 mL×3). The combined extracts was dried by MgSO4, and evaporated to give a brown oil which was chromatographed (silica gel; EtOAc: n-hexane=1:1) to afford Compound 1 (0.5 g, 72%) as a white solid.

Workup

  1. additionwas added over 10 min at room temperature
  2. stirringThe reaction mixture continued stirring for another 1 hr
  3. customThe reaction was quenched with H2O (10 ml)
  4. extractionextracted with CH2Cl2 (10 mL×3)
  5. dry with materialThe combined extracts was dried by MgSO4
  6. customevaporated
  7. customto give a brown oil which
  8. customwas chromatographed (silica gel; EtOAc: n-hexane=1:1)

Sources & evidence

ORD record
ord-cc5a257e6ec843168c453d24285ce386
Source dataset
uspto-grants-2009_05
Patent number
US07528165B2

Reaction notes

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