Cesium carbonate → Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-3-nitro-4-biphenylcarboxylate

HRID 2220397Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH2:15]([N:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:15]([N:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)=[CH:27][CH:26]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 4-chloro-2-nitrobenzoate (3.81 g) and [4-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-phenyl]boronic acid (6.91 g) in 1,4-dioxane (76 ml) were added cesium carbonate (8.64 g), potassium fluoride (3.08 g), tri-tert-butylphosphine (1.1 ml) and tris(dibenzylideneacetone)dipalladium(0) (1.62 g) under nitrogen at room temperature and then stirred at 80° C. for 3 hours. The mixture was diluted with ethyl acetate, filtrated through silica gel pad and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-3-nitro-4-biphenylcarboxylate (3.41 g).

Workup

filtrationfiltrated through silica gel pad
customevaporated
customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-dbcd9eb07553466581e1fe64df15a025
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417060B2

Reaction notes

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