Potassium Phosphate, Tribasic → Methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate

HRID 2283682Notes

Reaction equation

CB(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:13]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl[C:48]1[C:52]2[CH:53]=[C:54]([O:57][CH3:58])[CH:55]=[CH:56][C:51]=2[S:50][C:49]=1[C:59]([O:61][CH3:62])=[O:60]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:58][O:57][C:54]1[CH:55]=[CH:56][C:51]2[S:50][C:49]([C:59]([O:61][CH3:62])=[O:60])=[C:48]([CH3:13])[C:52]=2[CH:53]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl boronic acid (120 mg), potassium phosphate (849 mg), water (0.30 ml), palladium acetate (22 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl (95 mg) were added to a solution of methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate (257 mg) in 1,4-dioxane (3.0 ml), and the reaction solution was stirred at 100° C. for 12 hours. The reaction solution was diluted with ethyl acetate and washed successively with an aqueous ammonium chloride solution, an aqueous sodium bicarbonate solution, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate.

Workup

washwashed successively with an aqueous ammonium chloride solution
dry with materialAfter drying over anhydrous sodium sulfate
customthe solvent was evaporated under vacuum
customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record: ord-ade2f2939fc04385b686a0b1e7d7f253
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145414B2

Reaction notes

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