Benzyl Bromide → Methyl 4-(benzyloxy)-7-bromoisoquinoline-3-carboxylate

HRID 1481143Notes

Reaction equation

HRID 1481143 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([Br:16])[CH:9]=2)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH:23]1[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:29]([O:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([Br:16])=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4])[C:26]1[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 89813103Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

Product 1

HCID 89812966Methyl 4-(benzyloxy)-7-bromoisoquinoline-3-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (955.0 mg, 3.4 mmol), K2CO3 (1.2 g, 8.5 mmol), KI (56.2 mg, 0.3 mmol) and BnBr (0.6 mL, 4.7 mmol) in DMF (17 mL) was stirred at 60° C. for 16 hours. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL) and H2O (100 mL). The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-20% EtOAc/CH2Cl2) to give the title compound in 1.1 g. MS: (+) m/z 372.20 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-ee7ddeedfb2a4921a551f0fdb41a90dc
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…