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

HRID 415902Notes

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-531d4783b00b473bb36558c66d292a62
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088794B2

Reaction notes

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