Tetrafluoroboric acid → HCID 66803424, compound

HRID 1528303Notes

Reaction equation

HRID 1528303 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:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[C:18]([C:33]#[N:34])=[CH:17]2.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>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[C:33]([C:18]1[N:19]([Si:23]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:32])[CH3:31])[CH:24]([CH3:25])[CH3:26])[C:20]2[C:16]([CH:17]=1)=[CH:15][C:14]([N:10]1[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]1)=[CH:22][CH:21]=2)#[N:34]

Participants

8

Reactant 5

HCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 66800102HCID 66800102, compoundHCID 66803538HCID 66803538, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 66803424HCID 66803424, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A toluene (5 ml) suspension of (4aS,8aS)-2,2-dimethyldecahydroquinoxaline (200 mg, 1.19 mmol), 5-bromo-1-(triisopropylsilyl)-1H-indole-2-carbonitrile (493 mg, 1.31 mmol), Pd(OAc)2 (13.3 mg, 0.0594 mmol), tBu3P.HBF4 (17.2 mg, 0.0594 mmol), and t-BuONa (137 mg, 1.43 mmol) was stirred at 100° C. for 4 hours in a nitrogen atmosphere. Insoluble matter was filtered through celite, and the filtrate was concentrated. The obtained residue was purified by basic silica gel column chromatography (AcOEt/hexane) to obtain (4aS,8aS)-1-(2-cyano-1-(triisopropylsilyl)-1H-indol-5-yl) 3,3-dimethyldecahydroquinoxaline (430 mg, 78%) in a white amorphous solid form.

Workup

  1. filtrationInsoluble matter was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified by basic silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-be88f7189c8d47a893e337bcbd68a01f
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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