Water → HCID 178515622, compound

HRID 2222122Notes

Reaction equation

HRID 2222122 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-6124c6f687054c26a1978aa197f4daf9
Source dataset
uspto-grants-2008_05
Patent number
US07371752B2

Reaction notes

Loading…