N-Methylaniline → HCID 58557028, compound

HRID 469475Notes

Reaction equation

HRID 469475 reaction equation
[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.O=[CH:23][C:24]([OH:26])=[O:25]>C(#N)C>[S:1]1[CH:5]=[C:4]([CH:23]([N:14]([CH3:13])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:24]([OH:26])=[O:25])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58557028HCID 58557028, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of benzo[b]thiophen-3-ylboronic acid (300 mg, 1.68 mmol), N-methylaniline (184 μl, 1.68 mmol) and 2-oxoacetic acid hydrate (155 mg, 1.65 mmol) in acetonitrile (20 ml) was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the crude product was purified by flash chromatography (DCM/MeOH=95/5) to obtain 2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetic acid (351 mg, 70% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-290ac2887cb7451b8e976f942c565ff5
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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