8-Cyano-6-methoxynaphthalene-2-yl trifluoromethanesulfonate → 3-Methoxy-7-(3-methoxyphenyl)-1-naphthonitrile

HRID 1035609Notes

Reaction equation

HRID 1035609 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([C:19]#[N:20])[CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)(=O)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27](OB(O)O)[CH:28]=[CH:29][CH:30]=1>>[CH3:18][O:17][C:12]1[CH:11]=[C:10]([C:19]#[N:20])[C:9]2[C:14]([CH:13]=1)=[CH:15][CH:16]=[C:7]([C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([O:24][CH3:23])[CH:30]=1)[CH:8]=2

Participants

3

Reactant 2

HCID 111983248-Cyano-6-methoxynaphthalene-2-yl trifluoromethanesulfonateHCID 221738233-Methoxyphenylboric acid

Product 1

HCID 594434383-Methoxy-7-(3-methoxyphenyl)-1-naphthonitrileYield 25%

Procedure

The compound is prepared by the reaction of 8-cyano-6-methoxynaphthalene-2-yl trifluoromethanesulfonate (466 mg, 1.4 mmol, 1 eq) with 3-methoxyphenylboric acid (260 mg, 1.7 mmol, 1.2 eq) according to method A over night. Purification by column chromatography with hexane/ethyl acetate 7/3 as the eluent yielded the desired compound in a yield of 25%, 113 mg.

Workup

  1. waitaccording to method A over night
  2. customPurification by column chromatography with hexane/ethyl acetate 7/3 as the eluent

Sources & evidence

ORD record
ord-ac64b80ec8454639b359d5be9b4c95d4
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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