Tetrafluoroboric acid → HCID 66800342, compound

HRID 1528301Notes

Reaction equation

HRID 1528301 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:11][NH:10][C@@H:9]2[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.Br[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([Cl:22])[CH:15]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F.C(O[Na])(C)(C)C.Cl.CCOC(C)=O>C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[ClH:22].[Cl:22][C:16]1[CH:15]=[C:14]([N:10]2[C@@H:9]3[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]3)[NH:3][C:2]([CH3:12])([CH3:1])[CH2:11]2)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Participants

10

Reactant 6

HCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 70104204-Bromo-2-chlorobenzonitrileHCID 21866389Hydrogen chloride-ethyl acetateHCID 66800102HCID 66800102, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 66800342HCID 66800342, compoundYield 57.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A toluene (10 ml) suspension of (4aS,8aS)-2,2 -dimethyldecahydroquinoxaline (400 mg, 2.38 mmol), 4-bromo-2-chlorobenzonitrile (669 mg, 3.09 mmol), Pd(OAc)2 (53 mg, 0.24 mmol), t-Bu3P.HBF4 (70 mg, 0.24 mmol), and t-BuONa (320 mg, 3.33 mmol) was stirred for 5 hours under reflux in a nitrogen atmosphere. The reaction solution was cooled. Then, insoluble matter was filtered through celite, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (CH2Cl2/MeOH) to obtain an orange amorphous solid. This amorphous solid was dissolved in ethyl acetate (5 mL). A crystal deposited by the addition of 4 N HCl/AcOEt (0.6 mL) was collected by filtration and dried under reduced pressure to obtain (4aS,8aS)-1-(3-chloro-4-cyanophenyl)-3,3-dimethyldecahydroquinoxaline hydrochloride (304 mg, 48%) in a pale orange powder form.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere
  2. temperatureThe reaction solution was cooled
  3. filtrationThen, insoluble matter was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. customThe obtained residue was purified by silica gel column chromatography (CH2Cl2/MeOH)
  6. customto obtain an orange amorphous solid
  7. filtrationwas collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-b12cddc69ed34ad4b8e0fd77a123baa8
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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