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Piperidine → 3-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole

HRID 1178908
Notes
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Reaction equation

HRID 1178908 reaction equation
[N:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:8]=2)[CH2:6][CH2:5]O[CH2:3][CH2:2]1.Br[C:27]1C2C(=CC=CC=2)N([Si](C(C)C)(C(C)C)C(C)C)C=1.N1CCCCC1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[N:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:8]=2)[CH2:6][CH2:5][CH2:27][CH2:3][CH2:2]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8082PiperidineHCID 2733832Lithium hexamethyldisilazaneHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 109917693-Bromo-1-(triisopropylsilyl)indoleHCID 589751763-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 58974986
3-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Following a method similar to 3-morpholin-4-yl-1-triisopropylsilanyl-1H-indole using 3-bromo-1-triisopropylsilanyl-1H-indole (0.70 g, 1.99 mmol), piperidine (0.26 g, 3.04 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.02 g, 0.05 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.05 g, 0.05 mmol) and 1N solution of lithium bis(trimethylsilyl)amide in THF (2.40 mL) to prepare the title compound. Purify by flash chromatography using 0 to 40% of EtOAc in hexanes to give the title compound (0.20 g, 29%): MS (ES) 357.1 (M+1)+.

Sources & evidence

ORD record
ord-618f38a4a38c48c3b44e2ea6224ca97f
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07276516B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes