Sodium Acetate → HCID 22171537, compound

HRID 1866174Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:15]=1.C([O-])(=O)C.[Na+]>CN(C)C(=O)C.C(OCC)(=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:26]([O:25][C:23]([NH:22][CH2:21][CH2:20][C:16]1[CH:15]=[C:14]2[C:19]([C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[CH2:12][O:13]2)=[CH:18][CH:17]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of methyl 4-bromo-3-[[3-[2-[(tert-butoxycarbonyl)amino]ethyl]phenoxy]methyl]benzoate (410 mg) in N,N-dimethylacetamide (4.0 ml) was added dichlorobis(triphenylphosphine)palladium(II) (124 mg) and sodium acetate (362 mg), and the mixture was stirred at 130° C. for 1.5 hours under nitrogen. The mixture was cooled to room temperature, diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 3-[2-[(tert-butoxycarbonyl)amino]ethyl]-6H-benzo[c]chromene-8-carboxylate (190 mg).

Workup

temperatureThe mixture was cooled to room temperature
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-c4dfaca4f9ca4c6dae61f103fd21512d
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629366B2

Reaction notes

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