Diphenyl Ether → 3-[3-(Methyloxy)phenyl]thieno[2,3-b]pyridin-4(7H)-one

HRID 573566Notes

Reaction equation

HRID 573566 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[CH:15]=2)C(=O)O1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH3:23][O:22][C:18]1[CH:17]=[C:16]([C:14]2[C:15]3[C:6](=[O:8])[CH:5]=[CH:9][NH:10][C:11]=3[S:12][CH:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 672359842,2-Dimethyl-5-[({4-[3-(methyloxy)phenyl]-2-thienyl}amino)methylidene]-1,3-dioxane-4,6-dione

Product 1

HCID 683240213-[3-(Methyloxy)phenyl]thieno[2,3-b]pyridin-4(7H)-oneYield 56.7%

Conditions

Temperature
220 °C

Procedure

A mixture of 2,2-dimethyl-5-[({4-[3-(methyloxy)phenyl]-2-thienyl}amino)methylidene]-1,3-dioxane-4,6-dione (Description 41) (1.2 g, 3.34 mmol) and diphenyl ether (15 mL, 94 mmol) was heated at 220° C. for 1 h. After cooling to RT, the mixture was purified by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate in DCM, to give the title compound (487 mg). LCMS (A) m/z: 258 [M+1]+, Rt 0.93 min (acidic).

Workup

  1. temperatureAfter cooling to RT
  2. customthe mixture was purified by chromatography on silica
  3. washeluting with a gradient of 0-100% ethyl acetate in DCM

Sources & evidence

ORD record
ord-cb9fb66ac2644d13af9ef86728c0de1f
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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