Cesium carbonate → Methyl 7-(3-((2-fluoro-5-methylphenyl)carbamoyl)phenoxy)thieno[3,2-b]pyridine-2-carboxylate

HRID 525834Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1.Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:21]=12.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:21]=12)=[O:18]

Participants

Conditions

Temperature: 68 °C

Procedure

A mixture of N-(2-fluoro-5-methylphenyl)-3-hydroxybenzamide (270 mg, 1.1 mmol), methyl 7-chlorothieno[3,2-b]pyridine-2-carboxylate (300 mg, 1.3 mmol) and cesium carbonate (1.0 g, 3.07 mmol) in 10 ml of anhydrous DMSO was heated at 68° C. for 16 hours, cooled to room temperature and partitioned between water (100 ml) and EtOAc (100 ml). The aqueous layer was extracted with more EtOAc (2×50 ml). All the organic layers were combined, washed with brine (50 ml), dried over Na2SO4, and evaporated to dryness to give the crude, which was purified by silica gel chromatography eluted with 1˜2% of MeOH in CHCl3 to give methyl 7-(3-((2-fluoro-5-methylphenyl)carbamoyl)phenoxy)thieno[3,2-b]pyridine-2-carboxylate as light brown oil. Yield: 170 mg, 37%.

Workup

temperaturecooled to room temperature
custompartitioned between water (100 ml) and EtOAc (100 ml)
extractionThe aqueous layer was extracted with more EtOAc (2×50 ml)
washwashed with brine (50 ml)
dry with materialdried over Na2SO4
customevaporated to dryness
customto give the crude, which
customwas purified by silica gel chromatography
washeluted with 1˜2% of MeOH in CHCl3

Sources & evidence

ORD record: ord-886b02cba5bc41daa20bdd4d1c944825
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340555B2

Reaction notes

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