HCID 12751998, compound → HCID 21997827, compound

HRID 2205235Notes

Reaction equation

HRID 2205235 reaction equation
S([N:11]1[CH2:16][C:15](=[O:17])[C:14]2[S:18][CH:19]=[CH:20][C:13]=2[CH2:12]1)(C1C=CC(C)=CC=1)(=O)=O.CC([O-])(C)C.[K+]>OC(C)(C)C>[S:18]1[C:14]2[C:15](=[O:17])[CH2:16][N:11]=[CH:12][C:13]=2[CH:20]=[CH:19]1

Participants

4

Reactant 2

HCID 12751998HCID 12751998, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21997827HCID 21997827, compoundYield 178.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 5,6-dihydro-5-tosylthieno[3,2-c]pyridin-7(4H)-one (1.24 g, 4.03 mmol, 1.0 equiv) in HOt-Bu (15.0 mL) was added KOt-Bu (904 mg, 8.06 mmol, 2.0 equiv) and heated to reflux for 2 h. The mixture was quenched with water and then extracted with ethyl acetate. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 1.09 g of white solid, 89%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customPurification by column chromatography
  6. wash50% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-10fd11161bfb49b28cfab075769b61ac
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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