Ethanol → HCID 18472644, compound

HRID 1277319Notes

Reaction equation

HRID 1277319 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[CH2:10][CH2:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7][C:6]=2[CH:20]=1.B([O-])([O-])O[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH3:12])[CH2:10][CH2:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7][C:6]=3[CH:20]=2)=[CH:24][CH:25]=1)[CH3:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 18472450HCID 18472450, compoundHCID 86756168HCID 86756168, compound

Product 1

HCID 18472644HCID 18472644, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To t-butyl 7-bromo-1-methyl-2,3-dihydro-1-benzazepine-4-carboxylate (4.0 g), 4-ethoxyphenyl borate (2.35 g), 1M potassium carbonate solution (25 ml) and ethanol (25 ml) was added toluene (100 ml), and the mixture was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphine palladium (0.55 g), and the mixture was ref luxed under argon atmosphere overnight. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give t-butyl 7-(4-ethoxyphenyl)-1-methyl-2,3-dihydro-1-benzazepine-4-carboxylate (4.0 g) as yellow crystals.

Workup

  1. customwas ref luxed under argon atmosphere overnight
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customUnder reduced pressure, the solvent was evaporated
  5. customthe residue was purified with silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f478b1f8b7aa4f11b059312e66127b4c
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

Loading…