Triethylamine → 872625-35-9

HRID 507093Notes

Reaction equation

HRID 507093 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH2:7](N(CC)CC)C.I[C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][O:20][CH2:21]2)=[CH:17][C:16]=1[NH2:24].[C]=O>C(#N)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C(OCC)(=O)C>[CH3:7][O:2][C:1]([C:15]1[CH:23]=[C:22]2[C:18](=[CH:17][C:16]=1[NH2:24])[CH2:19][O:20][CH2:21]2)=[O:4]

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 594323366-Iodo-1,3-dihydroisobenzofuran-5-amineHCID 178418416HCID 178418416, compound

Product 1

HCID 59432335872625-35-9

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Add palladium (II) acetate (2.8 mmol), 1,1-bis(diphenylphosphino)ferrocene (2.8 mmol), potassium carbonate (86.1 mmol), and triethyl amine (28.7 mmol) to a solution of 6-iodo-1,3-dihydro-isobenzofuran-5-ylamine (28.7 mmol) in acetonitrile (150 mL) and methanol (75 mL). Using a balloon of carbon monoxide, vacuum purge the reaction mixture several times, then heat to 70° C. After heating under a balloon of carbon monoxide for 1.5 h, cool the reaction to room temperature. Dilute the reaction with ethyl acetate (500 mL), wash with water (3×100 mL), followed by brine. Dry the organic phase over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-35%) to provide the title compound as an off white solid. 1H NMR (CDCl3, 400 MHz) δ 3.85 (s, 3H), 4.97 (s, 4H), 6.54 (s, 1H), 7.71 (s, 1H).

Workup

  1. custompurge the reaction mixture several times
  2. temperatureAfter heating under a balloon of carbon monoxide for 1.5 h
  3. temperaturecool
  4. customthe reaction to room temperature
  5. additionDilute
  6. washwash with water (3×100 mL)
  7. dry with materialDry the organic phase over sodium sulfate
  8. filtrationfilter
  9. customremove the solvent under vacuum
  10. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-35%)

Sources & evidence

ORD record
ord-0c408d6515d548e4825ba845009f93ad
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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