Sodium Carbonate → N-({3-Chloro-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)cyclopropanamine

HRID 337581Notes

Reaction equation

HRID 337581 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:9][NH:10][CH:11]2[CH2:13][CH2:12]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CC1(C)C(C)(C)OB(/[CH:22]=[CH:23]/[CH2:24][O:25][CH3:26])O1.C(=O)([O-])[O-].[Na+].[Na+].[NH4+].[Cl-]>C(O)CC.CN(C=O)C>[Cl:8][C:6]1[CH:5]=[C:4]([CH2:9][NH:10][CH:11]2[CH2:13][CH2:12]2)[CH:3]=[C:2](/[CH:22]=[CH:23]/[CH2:24][O:25][CH3:26])[CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 67062055N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine

Product 1

HCID 66896177N-({3-Chloro-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)cyclopropanamine

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a 4:1 (v/v) DMF:n-propanol solution (0.15 M) of N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine (1 eq.) from the previous step and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (2 eq.) was added trans-dibromobis(triphenylphosphine) palladium(II) (0.05 eq.) followed by sodium carbonate (2 M aqueous solution, 3 eq.). The reaction vessel was evacuated and purged with nitrogen five times and then heated at 100° C. for 2 h. The cooled reaction mixture was poured into aq. sat. NH4Cl and then extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:7 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as an oil.

Workup

  1. customThe reaction vessel was evacuated
  2. custompurged with nitrogen five times
  3. customThe cooled reaction mixture
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 3:7 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-9037867b0bd548e89351912735b8423a
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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