Potassium Carbonate → HCID 9862584, compound

HRID 2306631Notes

Reaction equation

HRID 2306631 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[CH:14]=[CH:15][S:16][C:11]3=[C:10]([OH:17])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]3[CH:14]=[CH:15][S:16][C:11]3=[C:10]([O:17][CH2:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 178515622HCID 178515622, compound

Product 1

HCID 9862584HCID 9862584, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-fluorophenyl)-thieno[3,2-b]pyridin-7-ol (30 mg, 0.09 mmol), 2-picolyl chloride hydrochloride salt (30 mg) and potassium carbonate (100 mg) in DMF (2 mL) is heated at 100° C. for 2 hours. The reaction solution is cooled to room temperature, quenched with aqueous sodium bicarbonate solution and extracted several times with ethyl acetate. The combined ethyl acetate layers are dried over Na2SO4, filtered and concentrated. The residue is purified by preparative thin layer chromatography to give 5-(4-Fluorophenyl)-7-[(2-pyridyl)-methyloxy]-thieno[3,2-b]pyridine as white solid (compound 1).

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customquenched with aqueous sodium bicarbonate solution
  3. extractionextracted several times with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-2c4822315a694fa3b83cd2dca92dfa4d
Source dataset
uspto-grants-2004_12
Patent number
US06828329B2

Reaction notes

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