Water → HCID 178515622, compound

HRID 2306630Notes

Reaction equation

HRID 2306630 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, compound

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 in a flask equipped with a Dean-Stark water trap. The mixture is cooled to room temperature and the precipitate filtered and washed with diethyl ether. The solid is dissolved in diphenyl ether (80 mL) and heated at 240° C. for 2 hours. The reaction solution is then cooled to room temperature, diethyl ether added and the precipitate filtered and washed with diethyl ether to give 5-(4-fluorophenyl)-thieno[3,2-b]pyridin-7-ol as brown crystalline needles, m.p. 316-318° C.

Workup

  1. temperatureis refluxed for 20 hours in a flask
  2. filtrationthe precipitate filtered
  3. washwashed with diethyl ether
  4. dissolutionThe solid is dissolved in diphenyl ether (80 mL)
  5. temperatureheated at 240° C. for 2 hours
  6. temperatureThe reaction solution is then cooled to room temperature
  7. additiondiethyl ether added
  8. filtrationthe precipitate filtered
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7df7004ab5c849298afae3a10790fb60
Source dataset
uspto-grants-2004_12
Patent number
US06828329B2

Reaction notes

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