Benzeneacetic acid, alpha-bromo-, methyl ester → HCID 69354681, compound

HRID 458784Notes

Reaction equation

HRID 458784 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][CH:7]1[C:13]2[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=2[CH2:11][CH2:10][CH2:9][NH:8]1.Br[CH:28]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29]([O:31][CH3:32])=[O:30].CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:32][O:31][C:29](=[O:30])[CH:28]([N:8]1[CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[CH:7]1[CH2:6][C:5]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 122679961-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepineHCID 21226206Ethyl acetate hexane

Product 1

HCID 69354681HCID 69354681, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3,4-dimethoxy-benzyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine (1.10 g, 3.08 mmol), TEA (1.3 ml, 9.33 mmol), and methyl α-bromophenylacetate (487 μl, 3.09 mmol) in anhydrous toluene (13 ml) was stirred at reflux for 17 h under nitrogen. After cooling, the reaction mixture was dissolved in CH2Cl2 (40 ml), washed with H2O (15 ml), and the aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (AcOEt/hexane: 1/1) gave the title compound as a mixture of stereoisomers (1.34 g, 2.65 mmol, 86%, yellow oil).

Workup

  1. temperatureat reflux for 17 h under nitrogen
  2. temperatureAfter cooling
  3. washwashed with H2O (15 ml)
  4. extractionthe aqueous phase was extracted twice with CH2Cl2
  5. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil

Sources & evidence

ORD record
ord-41483652722c477c97f95f4379d5c93a
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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