Cesium carbonate → HCID 90308894, compound

HRID 2283674Notes

Reaction equation

[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[C:55]1[C:63]2[CH:62]=[CH:61][S:60][C:59]=2[CH:58]=[C:57]([C:64]([O:66][CH2:67][CH3:68])=[O:65])[CH:56]=1)(=O)=O>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:4]([O:3][C:1]([NH:2][C:55]1[C:63]2[CH:62]=[CH:61][S:60][C:59]=2[CH:58]=[C:57]([C:64]([O:66][CH2:67][CH3:68])=[O:65])[CH:56]=1)=[O:8])([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 100 °C

Procedure

Tert-butyl carbamate (81 mg), palladium acetate (4 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl (17 mg), and cesium carbonate (340 mg) were added to a solution of ethyl 4-(trifluoromethylsulfonyloxy)benzo[b]thiophene-6-carboxylate obtained in the above-described Step 2 (120 mg) in dioxane (2 ml), and the reaction solution was stirred at 100° C. for 3 hours. The reaction solution was diluted with ethyl acetate, and washed successively with a saturated aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain ethyl 4-(tert-butoxycarbonylamino)benzo[b]thiophene-6-carboxylate.

Workup

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

Sources & evidence

ORD record: ord-78cb130582a7486a931247f034ea4a16
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145414B2

Reaction notes

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