3-Fluoroaniline → HCID 58557019, compound

HRID 469508Notes

Reaction equation

HRID 469508 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].O.O=[CH:22][C:23]([OH:25])=[O:24]>C(#N)C>[F:12][C:13]1[CH:14]=[C:15]([NH:16][CH:22]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:23]([OH:25])=[O:24])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58557019HCID 58557019, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-methoxypyridin-3-ylboronic acid (200 mg, 1.31 mmol), 3-fluoroaniline (126 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-fluorophenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (48 mg, 13.3% 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-697aa3f34dc643538235bdf2f577e141
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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