Ethyl Acetate → HCID 59771162, compound

HRID 340570Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11](Br)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[C:20]1(B(O)O)[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([C:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=2)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-(3-bromo-4-nitro-phenyl)-malonic acid dimethyl ester (as prepared in the previous step, 300 mg, 0.903 mmol), cyclohexane-1-enyl boronic acid (125 mg, 0.994 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II)dichloromethane adduct (Pd(dppf)Cl2-CH2Cl2) (66.0 mg, 0.0903 mmol) in 5 mL of DMF was added K3PO4 (765 mg, 3.61 mmol). The resulting mixture was stirred at 60° C. for 9 h under Ar. After cooling to RT, the mixture was treated with 50 mL of EtOAc, washed with H2O (3×10 mL) and brine (10 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with 10% EtOAc-hexane to afford 210 mg (70%) of the title compound as a yellow oil: Mass spectrum (ESI, m/z): Calcd. for C17H19NO6, 334.1 (M+H). found 334.0.

Workup

temperatureAfter cooling to RT
washwashed with H2O (3×10 mL) and brine (10 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel with 10% EtOAc-hexane

Sources & evidence

ORD record: ord-5d94a6ba6ebf4bfab58a84d25bf511e3
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895584B2

Reaction notes

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