Hydrochloric Acid → HCID 10271436, compound

HRID 1797404Notes

Reaction equation

HRID 1797404 reaction equation
Br[C:2]1[C:3]([CH3:22])=[C:4]([CH3:21])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[C:6]=2[C:19]=1[CH3:20].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[Na])(C)(C)C.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH2:23]([NH:30][C:2]1[C:3]([CH3:22])=[C:4]([CH3:21])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[C:6]=2[C:19]=1[CH3:20])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 9924988HCID 9924988, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 10271436HCID 10271436, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Under a nitrogen atmosphere, to toluene (500 mL) were added 5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (100 g) and benzylamine (36.5 mL), then palladium acetate (62.5 mg) and 2,2′-bis(diphenylphosphinino)-1,1′-binaphthyl [(BINAP, 0.52 g)], and further t-BuONa (37.45 g). The mixture was stirred at 25° C. for 20 minutes and then at 107° C. for 24 hours. To the mixture were added dropwise 1N HCl (167 mL) and water (113 mL) at 70° C. or below, and the mixture was stirred for 10 minutes. The organic layer was separated and washed with a 10% aqueous sodium chloride solution, and the solvent was distilled off. The residue was crystallized from isopropanol-water to obtain the title compound (99 g, 92.3%).

Workup

  1. waitat 107° C. for 24 hours
  2. stirringthe mixture was stirred for 10 minutes
  3. customThe organic layer was separated
  4. washwashed with a 10% aqueous sodium chloride solution
  5. distillationthe solvent was distilled off
  6. customThe residue was crystallized from isopropanol-water

Sources & evidence

ORD record
ord-c3e48645739e49558b44dc0023e8e715
Source dataset
uspto-grants-2006_04
Patent number
US07034166B2

Reaction notes

Loading…