Diphenyl Ether → Thieno[3,2-b]pyridin-7-ol

HRID 415898Notes

Reaction equation

HRID 415898 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)C(=O)O1.C1(OC2C=CC=CC=2)C=CC=CC=1>CC(OC)(C)C>[S:13]1[C:12]2[C:11](=[N:10][CH:9]=[CH:5][C:6]=2[OH:8])[CH:15]=[CH:14]1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 222500872,2-Dimethyl-5-((thiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione

Product 1

HCID 5074765Thieno[3,2-b]pyridin-7-ol

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A 200-mL rb flask was charged with 2,2-dimethyl-5-((thiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione (6.73 g, 26.6 mmol) and diphenyl ether (25 mL) and heated to about 200 deg C. for about 30-45 min and the mixture was allowed to cool to rt overnight. The mixture was scraped down with a spatula and diluted with MTBE. The mixture was filtered through paper and washed with MTBE. The brown solid was air dried to yield thieno[3,2-b]pyridin-7-ol.

Workup

  1. temperatureheated to about 200 deg C
  2. filtrationThe mixture was filtered through paper
  3. washwashed with MTBE
  4. customdried

Sources & evidence

ORD record
ord-4713f4b7f0a749d6b58d3eab6ea48c2d
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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