Ethyl 3-aminobenzoate → 2-(3-(Ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid

HRID 469496Notes

Reaction equation

HRID 469496 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].O.O=[CH:26][C:27]([OH:29])=[O:28]>C(#N)C>[CH2:19]([O:18][C:16]([C:15]1[CH:14]=[C:13]([NH:12][CH:26]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:27]([OH:29])=[O:28])[CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 11400Ethyl 3-aminobenzoateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 585569882-(3-(Ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acidYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-methoxypyridin-3-ylboronic acid (1.2 g, 7.84 mmol), ethyl 3-aminobenzoate (1.29 g, 7.84 mmol), and 2-oxoacetic acid hydrate (723 mg, 7.84 mmol) in acetonitrile (70 ml) was stirred at room temperature overnight. The solvent was evaporated under vacuum, and the crude product was purified by flash chromatography (DCM/MeOH=9/1) to obtain 2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (0.95 g, 38% yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe crude product was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-8369962b561541e08ea1fbba3ee7323d
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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