Potassium Carbonate → Methyl 3-amino-4-(6-methoxyquinolin-2-yl)benzoate

HRID 2280477Notes

Reaction equation

HRID 2280477 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[NH2:14][C:15]1[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>COCCO.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:14][C:15]1[CH:20]=[C:19]([CH:18]=[CH:17][C:16]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 836472-Chloro-6-methoxyquinolineHCID 2737801(2-Amino-4-(methoxycarbonyl)phenyl)boronic acid

Product 1

HCID 66980049Methyl 3-amino-4-(6-methoxyquinolin-2-yl)benzoateYield 19%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 22504935Water 2-methoxyethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of compound 2-chloro-6-methoxyquinoline (1.70 g, 8.78 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid (2.05 g, 10.5 mmol), and K2CO3 (2.43 g, 17.6 mmol) in ethylene glycol monomethyl ether/H2O (35 mL/5 mL) was added Pd(dppf)Cl2 (158 mg, 0.193 mmol) under N2 atmosphere. Then the mixture was heated to 80° C. for 3 hours. After aqueous workup with EtOAc extraction, the resulting crude product was purified by silica gel column (PE/EtOAc=15/1 to 3/1) to give the product (500 mg, yield 19%) as a yellow solid.

Workup

  1. extractionAfter aqueous workup with EtOAc extraction
  2. customthe resulting crude product was purified by silica gel column (PE/EtOAc=15/1 to 3/1)

Sources & evidence

ORD record
ord-acc6f3c4897341db8e870168f0a347d9
Source dataset
uspto-grants-2015_09
Patent number
US09139528B2

Reaction notes

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