Aniline → 2-(Benzo[b]thiophen-7-yl)-2-(phenylamino)acetic acid

HRID 469469Notes

Reaction equation

HRID 469469 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9](B(O)O)[C:2]1=2.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.O=[CH:22][C:23]([OH:25])=[O:24]>CC#N>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:22]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:23]([OH:25])=[O:24])[C:2]1=2

Participants

5

Reactant 3

HCID 6115AnilineHCID 15620607Glyoxylic acid, monohydrateHCID 166405281-Benzothien-7-ylboronic acid

Product 1

HCID 585570382-(Benzo[b]thiophen-7-yl)-2-(phenylamino)acetic acidYield 63.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of benzo[b]thiophen-7-ylboronic acid (300 mg, 1.68 mmol), aniline (157 mg, 1.68 mmol), and 2-oxoacetic acid hydrate (155 mg, 1.68 mmol) in CH3CN (20 ml) was stirred at room temperature for 2 hours. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain 2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetic acid (303 mg, 63.5% yield).

Workup

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

Sources & evidence

ORD record
ord-b0b765b6764c4e89aa545c36aae88dc5
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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