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

HRID 1044043Notes

Reaction equation

HRID 1044043 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].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>[F:13][C:9]1[CH:8]=[C:7]([CH:2]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:3]([O:5][CH3:6])=[O:4])[CH:12]=[CH:11][CH:10]=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

Methyl 2-bromo-2-(3-fluorophenyl)acetate (I15) (300 mg, 1.21 mmol), DIPEA (0.32 ml, 1.82 mmol), and aniline (0.17 ml, 1.82 mmol) were dissolved in acetonitrile (4 ml) and heated under microwave irradiation at 100° C. for 1 hour. Acetonitrile was evaporated, and the residue was purified by flash chromatography (Petroleum ether/EtOAc=95/5) to obtain intermediate I16 (229 mg, 73% yield).

Workup

  1. customAcetonitrile was evaporated
  2. customthe residue was purified by flash chromatography (Petroleum ether/EtOAc=95/5)
  3. customto obtain intermediate I16 (229 mg, 73% yield)

Sources & evidence

ORD record
ord-414547ee2ea84c88a5c5cd6c97006ea9
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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