Water → HCID 178515622, compound

HRID 843658Notes

Reaction equation

HRID 843658 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.[F:10][C:11]1[CH:24]=[CH:23][C:14]([C:15]([CH2:17]C(OCC)=O)=O)=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:10][C:11]1[CH:24]=[CH:23][C:14]([C:15]2[N:1]=[C:2]3[CH:6]=[CH:5][S:4][C:3]3=[C:7]([OH:9])[CH:17]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 15124973-Amino-2-thiophenecarboxylic acidHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Product 1

HCID 178515622HCID 178515622, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-amino-2-thiophenecarboxylic acid (8 g, 49 mmol), ethyl 4-fluorobenzoylacetate (9.6 g, 49 mmol), and p-toluenesulfonic acid monohydrate (0.2 g, 1 mmol) in toluene (100 mL) is refluxed for 20 hours with a Dean-Stark water trap to remove produced water. After cooling to room temperature, the precipitate is filtered and washed with diethyl ether. The solid is dissolved in diphenyl ether (80 mL) and heated at 220° C. for 2 hours. The reaction solution is then cooled to room temperature, diethyl ether is added, and the precipitate is filtered and washed with diethyl ether to give 5-(4-fluorophenyl)-thieno[3,2-b]pyridin-7-ol (2 g, 17% yield) as brown crystalline needles, m.p. 316-318° C.

Workup

  1. customto remove
  2. customproduced water
  3. filtrationthe precipitate is filtered
  4. washwashed with diethyl ether
  5. dissolutionThe solid is dissolved in diphenyl ether (80 mL)
  6. temperatureheated at 220° C. for 2 hours
  7. temperatureThe reaction solution is then cooled to room temperature
  8. additiondiethyl ether is added
  9. filtrationthe precipitate is filtered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-acf98f066047491a84bf1db97b58db15
Source dataset
uspto-grants-2002_04
Patent number
US06380209B1

Reaction notes

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