1,2-Dibromoethane → HCID 69552004, compound

HRID 1833174Notes

Reaction equation

HRID 1833174 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9]([C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH3:29])[CH3:28])[CH:21]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:37][CH2:38][CH2:39]Br.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:16][CH2:39][CH2:38][Br:37])[CH:14]=2)[C:9]([C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH3:29])[CH3:28])[CH:21]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 136334117HCID 136334117, compound

Product 1

HCID 69552004HCID 69552004, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 6-hydroxy-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester (73 mg, 0.18 mmol) in N,N dimethylformamide (2 mL) was added potassium carbonate (197 mg, 1.42 mmol) and 1,2-dibromoethane (0.046 mL, 0.89 mmol) at room temperature. The reaction mixture was heated 85° C. for 2 hrs. The solvent was evaporated and the crude product was diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 30% ethyl acetate/hexane) afforded 6-(2-bromo-ethoxy)-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester as a white solid (70 mg, 75% yield).

Workup

  1. customThe solvent was evaporated
  2. additionthe crude product was diluted with ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a2e8794a064488fa5c11c9bf67b28a1
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

Loading…