Potassium Carbonate → Methyl 6-amino-3-bromo-2-carbamoylmethoxybenzoate

HRID 595124Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:12])[C:5]([Br:13])=[CH:4][CH:3]=1.Br[CH2:15][C:16]([NH2:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH2:15][C:16](=[O:17])[NH2:18])[C:5]([Br:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 6-amino-3-bromo-2-hydroxybenzoate (prepared according to Wang et al, Bioorg Med Chem Lett, 2007, 17, 2817, 7.55 g), bromoacetamide (4.55 g) and potassium carbonate (10.0 g) in DMF (70 mL) was heated to 60° C. for 17 hours. After cooling, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and water and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo to give an orange solid which was triturated with ether to give methyl 6-amino-3-bromo-2-carbamoylmethoxybenzoate (5.81 g) as a sandy coloured solid.

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in ethyl acetate
customwater and the layers were separated
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialthe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto give an orange solid which
customwas triturated with ether

Sources & evidence

ORD record: ord-63b3b2a5d99c4250871ae1d413e4ee55
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242997B2

Reaction notes

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