Water → 3-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester

HRID 1774794Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH2:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[CH3:22][O:23][C:24](=[O:27])[CH2:25]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:22][O:23][C:24](=[O:27])[CH2:25][CH:8]([C:6]1[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 6-bromo-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine (3.3 g, 9.0 mmol), bromo-acetic acid methyl ester (2.1 mL, 22.5 mmol) and K2CO3 (8.4 g, 60.8 mmol) were suspended in DMF (18.0 mL) and stirred at 40° C. for 1 hour before pouring into water (50 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 3-(6-bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester (3.9 g, quant.) as a light yellow solid. MS: 443.1 & 445.1 (M+H+).

Workup

extractionAfter extraction with EtOAc
washthe organic layer was washed with brine
customdried over anhy
filtrationNa2SO4, filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a956254c86434a9a81d900c41aec0604
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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