Water → 6-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3']bipyridinyl-5'-carboxylic acid methyl ester

HRID 1774795Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH:5]([C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18](Br)[N:17]=1)S(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:33][O:34][C:35]([C:37]1[CH:38]=[N:39][CH:40]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:42]=1)=[O:36].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:33][O:34][C:35]([C:37]1[CH:42]=[C:41]([C:18]2[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([CH:5]=[CH:4][C:3]([O:2][CH3:1])=[O:26])[N:17]=2)[CH:40]=[N:39][CH:38]=1)=[O:36]

Participants

Conditions

Temperature: 120 °C

Procedure

3-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester (1.2 g, 2.7 mmol), Pd(PPh3)2Cl2 (190 mg, 0.27 mmol), Na2CO3 (572 mg, 5.4 mmol) and 3-(methoxycarbonyl)pyridine-5-boronic acid pinacol ester (926 mg, 3.5 mmol) were dissolved in 1,4-dioxane (4.0 mL) and the resulting reaction mixture was heated at 120° C. for 3 hours before it was poured into H2O (50 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 6-(2-methoxycarbonyl-vinyl)-5-nitro-[2,3′]bipyridinyl-5′-carboxylic acid methyl ester (926 mg, quant.) as a light yellow solid. MS: 344.1 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-01f413874ecd41a8bead1a0768eafa0f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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