3-Bromo-7-methoxyquinoline → 7-Methoxy-3-(3-methoxyphenyl)quinoline

HRID 1035599Notes

Reaction equation

HRID 1035599 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](OB(O)O)[CH:19]=[CH:20][CH:21]=1>>[CH3:13][O:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH3:14])[CH:21]=3)[CH:3]=[N:4]2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 187885483-Bromo-7-methoxyquinolineHCID 221738233-Methoxyphenylboric acid

Product 1

HCID 248274327-Methoxy-3-(3-methoxyphenyl)quinolineYield 76%

Procedure

The compound is prepared by the reaction of 3-bromo-7-methoxyquinoline (255 mg, 1.07 mmol, 1.06 eq) and 3-methoxyphenylboric acid (154 mg, 1.01 mmol, 1 eq) according to method A in 4.5 h. Purification by column chromatography with a mixture of hexane/ethyl acetate 9/1 yields the desired product in a yield of 76% (215 mg).

Workup

  1. customPurification by column chromatography
  2. additionwith a mixture of hexane/ethyl acetate 9/1

Sources & evidence

ORD record
ord-6410e7deb4224e908420774720bc98be
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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