HCID 71252214, compound → HCID 86676755, compound

HRID 2411162Notes

Reaction equation

HRID 2411162 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1>C(OCC)(=O)C.C(O)C.[C].[Pd]>[NH2:14][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:1]2[CH2:3][CH2:2]2)[CH:13]=1

Participants

5

Reactant 1

HCID 71252214HCID 71252214, compound

Product 1

HCID 86676755HCID 86676755, compoundYield 76.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 2-bromo-4-nitrobenzoate (871 mg), bis(tricyclohexylphosphine)palladium(II)dichloride (136 mg), tripotassium phosphate (3.98 g) and cyclopropylboronic acid (863 mg) were added toluene (10 mL) and water (0.4 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer, and the obtained residue was purified by column chromatography (ethyl acetate:hexane) to give methyl 2-cyclopropyl-4-nitrobenzoate (285 mg). The obtained methyl 2-cyclopropyl-4-nitrobenzoate (285 mg) was dissolved in a solution of ethyl acetate and ethanol, and catalytic hydrogenation was performed using palladium carbon to give methyl 4-amino-2-cyclopropylbenzoate (189 mg). Using the obtained methyl 4-amino-2-cyclopropylbenzoate (189 mg) and 3-chloropropane-1-sulfonyl chloride (0.156 mL) and by the reaction and treatment in the same manner as in Preparation Example 17, the title compound (168 mg) was obtained.

Sources & evidence

ORD record
ord-dba6758934c444c89d335225a3b84717
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…