Sodium Carbonate → Methyl 4'-[2-[[(benzyloxy)carbonyl]amino]ethyl]-2-methyl-1,1'-biphenyl-4-carboxylate

HRID 1866153Notes

Reaction equation

C([N:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)[C:9](=[O:11])[O-:10])C1C=CC=CC=1.[CH3:21][O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[C:27]([CH3:34])[CH:26]=1)=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([O:10][C:9]([NH:8][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:28]2[CH:29]=[CH:30][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:26][C:27]=2[CH3:34])=[CH:18][CH:19]=1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-benzyl-N-[2-(4-bromophenyl)ethyl]-carbamate (1.3 g) in 1,2-dimethoxyethane (20 ml) was added [4-(methoxycarbonyl)-2-methylphenyl]boronic acid (792 mg), tetrakis(triphenylphosphine)palladium (360 mg) and aqueous solution of sodium carbonate (2M, 4.1 ml), and the mixture was stirred at 80° C. for 2 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[[(benzyloxy)carbonyl]amino]ethyl]-2-methyl-1,1′-biphenyl-4-carboxylate (660 mg).

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-456ed9fa9a044f8fb8855436f626133f
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629366B2

Reaction notes

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