Potassium Carbonate → 2(1H)-Isoquinolinecarboxylic acid, 6-(cyclopropylmethoxy)-3,4-dihydro-4-hydroxy-, 1,1-dimethylethyl ester

HRID 524011Notes

Reaction equation

HRID 524011 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 117998818HCID 117998818, compound

Product 1

HCID 1179988792(1H)-Isoquinolinecarboxylic acid, 6-(cyclopropylmethoxy)-3,4-dihydro-4-hydroxy-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.50 g (5.65 mmol) 4,6-Dihydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example XLII), 840 mg (6.22 mmol) (bromomethyl)cyclopropane and 1.60 g (11.3 mmol) K2CO3 in 10 mL DMF are stirred at 80° C. over night. The reaction mixture is diluted with water and extracted with DCM. The organic layer is concentrated by evaporation and the residue is purified by HPLC.

Workup

  1. customare stirred at 80° C. over night
  2. extractionextracted with DCM
  3. concentrationThe organic layer is concentrated by evaporation
  4. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-ca09cf2e90624af1b8832ff2e252fe66
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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