Aniline → Methyl 2-(3-fluorophenyl)-2-(phenylamino)acetate

HRID 77021Notes

Reaction equation

HRID 77021 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1.CCN(C(C)C)C(C)C.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 57495616Methyl 2-bromo-2-(3-fluorophenyl)acetate

Product 1

HCID 54889725Methyl 2-(3-fluorophenyl)-2-(phenylamino)acetateYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Bromo-(3-fluoro-phenyl)-acetic acid methyl ester (I96) (300 mg, 1.21 mmol), DIPEA (0.32 mL, 1.82 mmol), and aniline (0.17 mL, 1.82 mmol) are dissolved in acetonitrile (4 mL) and heated under MW irradiation at 100° C. for 1 hour. Acetonitrile is evaporated and the residue is purified by flash chromatography (Petroleum ether/EtOAc=95/5) to obtain intermediate I145 as a colorless oil (229 mg, 73% yield).

Workup

  1. customAcetonitrile is evaporated
  2. customthe residue is purified by flash chromatography (Petroleum ether/EtOAc=95/5)

Sources & evidence

ORD record
ord-9b616f7e11884e658da0129c20bc1b7d
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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