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

HRID 1255054Notes

Reaction equation

HRID 1255054 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-af497e2d0aa240a1bfd501d208f5312f
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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