Potassium Carbonate → 6-Amino-7-methyl-quinoline-5-carboxylic acid methyl ester

HRID 245650Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[C:13](Br)[C:14]=1[NH2:15])=[O:4].[C:17]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[C:13]([CH3:17])[C:14]=1[NH2:15])=[O:4]

Participants

Conditions

Temperature: 180 °C

Procedure

To 1.59 g (5.66 mmol) of 6-amino-7-bromo-quinoline-5-carboxylic acid methyl ester in 30 mL of dioxane under an atmosphere of argon is added 2.35 g (17.0 mmol) of K2CO3, 323 mg (0.28 mmol) of tetrakis(triphenylphsophine)palladium and 710 mg (5.66 mmol) of trimethylboroxine. The reaction mixture is stirred in a microwave oven at 180° C. for 10 minutes. After filtration over Celite and concentration in vacuo, the residue is purified by flash chromatography (SiO2, ethyl acetate) y to afford 550 mg of product (45%) as a yellowish solid; LC/MS:217/218 (M+H)+.

Workup

filtrationAfter filtration
concentrationover Celite and concentration in vacuo
customthe residue is purified by flash chromatography (SiO2, ethyl acetate) y

Sources & evidence

ORD record: ord-65f1aba882184381bb7fd0efcba120e7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658801B2

Reaction notes

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