Methanol → HCID 59548677, compound

HRID 1914534Notes

Reaction equation

HRID 1914534 reaction equation
Br[C:2]1[C:7]2[CH2:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[NH:11][CH2:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:17]([O-:20])(=[O:19])C.[K+].[CH3:22]O>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:22][O:20][C:17]([C:2]1[C:7]2[CH2:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[NH:11][CH2:12][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:19]

Participants

6

Reactant 3

HCID 887MethanolHCID 517044Potassium AcetateHCID 49780356HCID 49780356, compound

Product 1

HCID 59548677HCID 59548677, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 10-bromo-6,11-dihydro-5H-dibenzo[b,e]azepine (0.008 mol), potassium acetate (4 g), Pd(OAc)2 (0.04 g) and 1,1′-(1,3-propanediyl)bis[1,1-d]phenyl-phosphine (0.16 g) in methanol (100 mL) and THF (100 mL) was placed in a pressure reactor and pressurized with CO gas up to 50 kg/square cm. The reaction mixture was heated at 125° C. for 16 hours, then cooled, filtered over dicalite, and the solvent was evaporated. The residue was partitioned between CH2Cl2 and water. The organic layer was dried over MgSO4, filtered, and the filtrate concentrated. The residue was purified by column chromatography over silica gel using CH2Cl2 as an eluent. The desired fractions were collected and the solvent was evaporated, yielding 1.86 g of the desired compound.

Workup

  1. customwas placed in a pressure reactor
  2. temperaturecooled
  3. filtrationfiltered over dicalite
  4. customthe solvent was evaporated
  5. customThe residue was partitioned between CH2Cl2 and water
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customThe residue was purified by column chromatography over silica gel
  10. customThe desired fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2709d07aa9824705bc96f25e9736a059
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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