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

HRID 736971
Notes
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Reaction equation

HRID 736971 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-486366c11e7a4adf9adea29da3c07271
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07595339B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes