3-Chloropropanesulphonyl chloride → HCID 71251875, compound

HRID 2411163Notes

Reaction equation

HRID 2411163 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:12]2[CH2:14][CH2:13]2)[CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20]>>[CH:12]1([C:4]2[CH:3]=[C:2]([N:1]3[CH2:16][CH2:17][CH2:18][S:19]3(=[O:21])=[O:20])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 86676755HCID 86676755, compound

Product 1

HCID 71251875HCID 71251875, compound

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.

Workup

  1. customby the reaction and treatment in the same manner
  2. customas in Preparation Example 17

Sources & evidence

ORD record
ord-9ea8f6d794ef42adbf2d598a6423f6e9
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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