Potassium Carbonate → HCID 69551692, compound

HRID 1833173Notes

Reaction equation

HRID 1833173 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[CH2:38][CH2:39][CH2:40][OH:41]>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][CH2:38][CH2:39][CH2:40][OH:41])[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 136334117HCID 136334117, compound

Product 1

HCID 69551692HCID 69551692, compoundYield 99.6%

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 (30 mg, 0.073 mmol) in N,N-dimethylformamide (1 mL) was added potassium carbonate (81.1 mg, 0.58 mmol) and 3-bromo-1-propanol (0.033 mL, 0.22 mmol) at room temperature. The reaction mixture was heated 85° C. for 2 hrs. The solvent was evaporated and the residue was purified on a flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane) to afford product 6-(3-hydroxy-propoxy)-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester as a colorless oil (34 mg, 99% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-57ba27a871754500951491e94da41f99
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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