4-Fluoro-N-methylaniline → Ethyl 2-((4-fluorophenyl)(methyl)amino)-2-phenylacetate

HRID 1044035Notes

Reaction equation

HRID 1044035 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.Br[CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].CCN(C(C)C)C(C)C>C(#N)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 680244-Fluoro-N-methylanilineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 58556946Ethyl 2-((4-fluorophenyl)(methyl)amino)-2-phenylacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-N-methylaniline (0.33 g, 2.67 mmol) was added to a solution of ethyl 2-bromo-2-phenylacetate (0.36 ml, 2.06 mmol) in acetonitrile (6.86 ml) and DIPEA (0.47 ml, 2.67 mmol). The dark solution was stirred at 100° C. under microwave irradiation for 1 hour. Then solvent was evaporated and the crude was purified by flash chromatography (Petroleum ether/EtOAc=97/3) to obtain intermediate I5 (0.59 g, 100% yield).

Workup

  1. customThen solvent was evaporated
  2. customthe crude was purified by flash chromatography (Petroleum ether/EtOAc=97/3)
  3. customto obtain intermediate I5 (0.59 g, 100% yield)

Sources & evidence

ORD record
ord-a072d791a82a4ecc9e353a444af539d7
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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