Potassium Carbonate → HCID 57597414, compound

HRID 1786389Notes

Reaction equation

HRID 1786389 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)[CH3:2].[NH2:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][N:20]=[CH:21]2)=[CH:16][CH:15]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][N:20]=[CH:21]2)=[CH:16][CH:15]=1)[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80186Ethyl 2-bromobenzoateHCID 634876Binap, (A+-)-HCID 14660277Isoquinolin-7-amine

Product 1

HCID 57597414HCID 57597414, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-bromo-benzoic acid ethyl ester (458 mg, 2.0 mmol), 7-aminoisoquinoline (144 mg, 1.0 mmol), Pd(OAc)2 (11 mg), BINAP (30 mg) and K2CO3 (414 mg) in 1 mL of toluene in a sealed tube was stirred for 16 h at 105° C. The reaction mixture was then allowed to cool to RT, diluted with 20 ml of CH2Cl2, filtered through a Celite® packed funnel and concentrated under reduced pressure. The concentrate was purified by flash column chromatography. The titled compound was obtained as oil. MS (ES+): 293.3 (M+H)+. Calc'd for C18H16N2O2—292.

Workup

  1. temperatureto cool to RT
  2. filtrationfiltered through a Celite®
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was purified by flash column chromatography

Sources & evidence

ORD record
ord-a4374f3946a54cfc9e1bff7fdf7f9ebf
Source dataset
uspto-grants-2009_03
Patent number
US07507748B2

Reaction notes

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