Cesium carbonate → Methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate

HRID 525827Notes

Reaction equation

HRID 525827 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12.[NH2:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.CCOC(C1C(=O)CCCC1)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu]Cl>[NH2:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 115683-AminophenolHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

Product 1

HCID 117690318Methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 7-chlorothieno[3,2-b]pyridine-2-carboxylate (500 mg, 2.20 mmol), 3-aminophenol (330 mg, 3.0 mmol), ethyl 2-cyclohexanonecarboxylate (73 mg, 0.43 mmol), copper(I) chloride (22 mg, 0.22 mmol) and cesium carbonate (1.48 g, 4.55 mmol) in 20 ml of anhydrous DMSO was placed in a 50 ml pressure tube, flushed with nitrogen, sealed and heated at 70° C. for 3 hours. The mixture was cooled to room temperature and poured into 100 ml of water. The precipitates were filtered, washed with water and dried to give crude methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate as brown solid. Yield: 330 mg.

Workup

  1. customwas placed in a 50 ml pressure tube
  2. customflushed with nitrogen
  3. customsealed
  4. temperatureThe mixture was cooled to room temperature
  5. additionpoured into 100 ml of water
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-73a3476223924543b82e1e35f2ff9e29
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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