3-Ethylaniline → HCID 58556982, compound

HRID 469505Notes

Reaction equation

HRID 469505 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[CH2:12]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH3:13].O.O=[CH:23][C:24]([OH:26])=[O:25]>C(#N)C>[CH2:12]([C:14]1[CH:15]=[C:16]([NH:17][CH:23]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:24]([OH:26])=[O:25])[CH:18]=[CH:19][CH:20]=1)[CH3:13]

Participants

5

Reactant 3

HCID 114753-EthylanilineHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58556982HCID 58556982, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-methoxypyridin-3-ylboronic acid (200 mg, 1.31 mmol), 3-ethylaniline (163 μl, 1.31 mmol), and 2-oxoacetic acid hydrate (120 mg, 1.31 mmol) in acetonitrile (20 ml) was stirred at room temperature overnight. The solvent was evaporated, and the crude product was purified by flash-chromatography (DCM/MeOH=9/1) to obtain 2-(3-ethylphenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (265 mg, 70.8% yield).

Workup

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

Sources & evidence

ORD record
ord-8c815f8bb55640af904b2b7c52214132
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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