Toluene → 7-Chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridine

HRID 2359687Notes

Reaction equation

HRID 2359687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13]/[N:14]=[C:15](\[NH2:17])/[CH3:16])=O)[S:10][C:3]=12.C1(C)C=CC=CC=1.ClC1C=CN=C2C=C(C(O)=O)SC=12>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[O:13][N:14]=[C:15]([CH3:16])[N:17]=3)[S:10][C:3]=12

Participants

5

Reactant 3

HCID 1140TolueneHCID 112760337-Chlorothieno[3,2-b]pyridine-2-carboxylic acidHCID 59598395[(Z)-1-aminoethylideneamino] 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 594273557-Chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridineYield 43.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

A 50 mL round bottom flask with a reflux condenser was charged with (1Z)—N′-(((7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl)oxy)ethanimidamide (0.282 g, 1.04 mmol) and toluene (10 ml) and heated to 110° C. and stirred for 18 hours. LC/MS analysis indicated a mixture of the product and 7-chlorothieno[3,2-b]pyridine-2-carboxylic acid. The reaction was diluted with chloroform (30 mL) and washed with water (30 mL), sat. aq. NaHCO3 (30 mL), and brine (30 mL). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to yield 7-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridine (0.1128 g, 43% yield) as a light yellow solid, which was used without further purification.

Workup

  1. washwashed with water (30 mL), sat. aq. NaHCO3 (30 mL), and brine (30 mL)
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa9fb59b23f64b51ab00933fcde482f4
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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