Dichloromethane → HCID 67517293, compound

HRID 2173209Notes

Reaction equation

HRID 2173209 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[CH:10][C:5]=2[CH2:4][O:3]1.[CH2:26](Cl)Cl>CC([O-])=O.CC([O-])=O.[Pd+2]>[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]3[CH2:26][CH:12]3[N:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86693005HCID 86693005, compound

Product 1

HCID 67517293HCID 67517293, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a solution of tert-butyl 4-[(E)-2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethenyl]piperazine-1-carboxylate (1.1 g, 3 mmol) in 30 mL of DCM was added Pd(OAc)2 (100 mg) and was cooled by ice/water. 50 mL of newly prepared CH2N2 solution was added dropwise. The reaction was warmed to room temperature and stirred over night. The solid was filtered off, and the filtrate was evaporated at reduced pressure to get crude product, which was purified via prep-HPLC to afford tert-butyl 4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)cyclopropyl]piperazine-1-carboxylate.

Workup

  1. addition50 mL of newly prepared CH2N2 solution was added dropwise
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated at reduced pressure
  4. customto get crude product, which
  5. customwas purified via prep-HPLC

Sources & evidence

ORD record
ord-86597c0a22db48318c6cb9de1a3dcd19
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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