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

HRID 2266359Notes

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

Conditions

Temperature: 110 °C

Procedure

A 50 mL round bottom flask with a reflux condenser was charged with (1 Z)—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

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

Sources & evidence

ORD record: ord-87cfe514a8b0426c850766d9635297ca
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858623B2

Reaction notes

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