Potassium Phosphate, Tribasic → 1-Cyclopropyl-isoquinoline-3-carboxylic acid methyl ester

HRID 334023Notes

Reaction equation

HRID 334023 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Cl)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH:16]2[CH2:18][CH2:17]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 15531562Methyl 1-chloroisoquinoline-3-carboxylate

Product 1

HCID 866882541-Cyclopropyl-isoquinoline-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 481 mg (2.17 mmol) 1-chloro-isoquinoline-3-carboxylic acid methyl ester, 235 mg (2.74 mmol) cyclopropylboronic acid, 100 mg (0.137 mmol) 1,1′-bis(diphenyl-phosphino)ferrocenedichloropalladium(II) and 950 mg (4.47 mmol) potassium phosphate in 20 mL dioxane was stirred at 110° C. for 12 h. The mixture was diluted with EtOAc, filtered over Celite and activated carbon and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=3/1).

Workup

  1. filtrationfiltered over Celite and activated carbon
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified by flash chromatography (PE/EtOAc=3/1)

Sources & evidence

ORD record
ord-83cadb7270eb4b72a32808716d2d66cc
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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