Sulfuric acid magnesium salt (1:1) → HCID 66800091, compound

HRID 1528297Notes

Reaction equation

HRID 1528297 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[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]([F:23])=[CH:16][CH:15]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F.CC([O-])(C)C.[Na+].[O-]S([O-])(=O)=O.[Mg+2]>CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O.O.C1(C)C=CC=CC=1>[F:23][C:17]1[C:18]2[O:22][CH:21]=[CH:20][C:19]=2[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:15][CH:16]=1

Participants

11

Reactant 6

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 22810137HCID 22810137, compoundHCID 23676156Sodium t-butoxideHCID 668005644-bromo-7-fluorobenzofuran

Product 1

HCID 66800091HCID 66800091, compoundYield 55.3%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A toluene (4 ml) suspension of (4aR,8aS)-2,2-dimethyldecahydroquinoxaline (168 mg, 0.998 mmol), 4-bromo-7-fluorobenzofuran (258 mg, 1.20 mmol), Pd(OAc)2 (11.2 mg, 0.0499 mmol), t-Bu3P.HBF4 (14.5 mg, 0.0500 mmol), and NaOt-Bu (135 mg, 1.40 mmol) was stirred for 4 hours under reflux in a nitrogen atmosphere. The reaction solution was cooled to room temperature. Then, water (0.5 mL) and AcOEt (10 mL) were added thereto, and the mixture was stirred. MgSO4 was further added thereto, and the mixture was stirred. Insoluble matter was filtered, and the residue was washed with AcOEt (5 ml×2). Then, the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (Hex-AcOEt) to obtain a colorless oil (167 mg). This oil was crystallized from hexane (1 mL) to obtain (4aS,8aR)-1-(7-fluorobenzofaran-4-yl)-3,3-dimethyldecahydroquinoxaline (107 mg, yield: 35%) in a white powder form.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere
  2. stirringthe mixture was stirred
  3. filtrationInsoluble matter was filtered
  4. washthe residue was washed with AcOEt (5 ml×2)
  5. concentrationThen, the filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (Hex-AcOEt)

Sources & evidence

ORD record
ord-fdfec454dbe14f85840db6e0cde73515
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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