Potassium Carbonate → Methyl 2-(4-chloro-5-iodo-2-methoxyphenylamino)propanoate

HRID 588856Notes

Reaction equation

C([C:5]1[C:6]([O:14][CH3:15])=[C:7]([NH2:13])[CH:8]=[C:9]([I:12])[C:10]=1[Cl:11])(C)(C)C.Br[CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:11][C:10]1[C:9]([I:12])=[CH:8][C:7]([NH:13][CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[C:6]([O:14][CH3:15])[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 4-chloro-5-iodo-2-methoxybenzenamine (2 g, 7.07 mmol), methyl 2-bromopropanoate (1.17 g, 7.07 mmol), K2CO3 (1.94 g, 14.14 mmol) and KI (0.235 g, 1.414 mmol) in DMF (25 mL) was stirred at 100° C. for 16 h. The mixture was allowed to cool to RT, quenched with aqueous NaHCO3 solution and then extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1:20) to afford the desired product (1.12 g, 43% yield) as a yellow solid. ESI-MS m/z: 370.1[M+H]+.

Workup

temperatureto cool to RT
customquenched with aqueous NaHCO3 solution
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1:20)

Sources & evidence

ORD record: ord-2e8e470483524951a5a5c8a6bedf958e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

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