Dimethylformamide → 3-Fluoro-4-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

HRID 2359688Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[O:15][N:14]=[C:13]([CH3:16])[N:12]=3)[S:10][C:3]=12.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>C(Cl)(Cl)Cl>[F:25][C:20]1[CH:19]=[C:18]([NH2:17])[CH:23]=[CH:22][C:21]=1[O:24][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[O:15][N:14]=[C:13]([CH3:16])[N:12]=3)[S:10][C:3]=12

Participants

Conditions

Temperature: 90 °C

Procedure

A 15 mL sealed tube was charged with 7-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridine (0.113 g, 0.449 mmol), 4-amino-2-fluorophenol (0.071 g, 0.56 mmol), cesium carbonate (0.512 g, 1.57 mmol), and DMF (2.00 ml) and sealed. The reaction mixture was stirred at 90° C. for 18 hours, allowed to cool to room temperature, then diluted with chloroform (50 mL) and washed with water (50 mL), sat. aq. NaHCO3 (50 mL), and brine (50 mL). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to yield a black solid. The product was purified by silica gel chromatography eluting with 3% methanol in methylene chloride to yield 3-fluoro-4-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine (0.074 g, 48% yield) as a yellow solid.

Workup

customA 15 mL sealed tube
customsealed
temperatureto cool to room temperature
washwashed with water (50 mL), sat. aq. NaHCO3 (50 mL), and brine (50 mL)
dry with materialThe organic layer was dried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto yield a black solid
customThe product was purified by silica gel chromatography
washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record: ord-f02fb9a135e6458689051e73607bfe61
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685983B2

Reaction notes

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