Benzyl chloroformate → HCID 67294469, compound

HRID 589204Notes

Reaction equation

HRID 589204 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:11])[CH2:10][CH2:9]2)=[C:4]([F:12])[CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11][C:23](=[O:24])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:9][CH2:10]2)=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 67294860HCID 67294860, compound

Product 1

HCID 67294469HCID 67294469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 1-(4-bromo-2-fluorophenyl)cyclopropanamine (2.16 mmol) in DCM (10 mL) at 0° C., was added DIEA (0.75 mL, 4.32 mmol) and benzyl chloroformate (0.37 mL, 2.59 mmol). The reaction mixture was warmed to it and stirred for 1 h until LC/MS analysis indicated the reaction was complete. The reaction was quenched with HCl (1N) and extracted with DCM. Drying over MgSO4, yielded crude product which was purified by flash chromatography (gradient EtOAc/Hexanes (0-50%). HPLC-MS tR=1.31 min (UV254 nm); mass calculated for formula C17H15BrFNO2 363.02, observed LCMS m/z 363.9 (M+H)

Workup

  1. temperatureThe reaction mixture was warmed to it
  2. customThe reaction was quenched with HCl (1N)
  3. extractionextracted with DCM
  4. dry with materialDrying over MgSO4
  5. customyielded crude product which
  6. customwas purified by flash chromatography (gradient EtOAc/Hexanes (0-50%)

Sources & evidence

ORD record
ord-38f811d935f84c3fa495c7d81b098a30
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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