Dichloromethane → Ethyl 3-(isopropylamino)benzoate

HRID 400529

Reaction equation

P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH:21]([NH2:24])([CH3:23])[CH3:22].ClCCl>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:21]([NH:24][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 160 °C

Procedure

Potassium phosphate (1.38 g, 6.5 mmol), palladium(II) acetate (56 mg, 0.25 mmol), and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine (139 mg, 0.25 mmol) were combined in a microwave tube under nitrogen. Ethyl 3-bromobenzoate (1.145 g, 5 mmol) in dimethoxyethane (2 mL) and isopropylamine (385 mg, 6.5 mmol) in dimethoxyethane (2 mL) were added. The tube was filled with nitrogen again. The tube was then capped, and the reaction mixture was heated in a microwave oven (Biotage Initiator™ 2.0, 0 to 100 watts) with stirring at 160° C. for 70 minutes. Then dichloromethane was added, and the crude mixture was filtered. The filtrate was concentrated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate=7:1) to give ethyl 3-(isopropylamino)benzoate.

Workup

additionThe tube was filled with nitrogen again
customThe tube was then capped
temperaturethe reaction mixture was heated in a microwave oven (Biotage Initiator™ 2.0, 0 to 100 watts)
filtrationthe crude mixture was filtered
concentrationThe filtrate was concentrated
customThe residue was purified by chromatography on silica gel (hexane/ethyl acetate=7:1)

Sources & evidence

ORD record: ord-298c13724bb8494f8703f9520bb511b1
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741899B2

Linked notes

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