1-Methylpiperazine → 3-(4-Methyl-piperazin-1-yl)-1-triisopropylsilanyl-1H-indole

HRID 1178907Notes

Reaction equation

HRID 1178907 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.BrC1C2C(=CC=CC=2)[N:29]([Si](C(C)C)(C(C)C)C(C)C)[CH:28]=1.CN1CCNCC1.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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>[CH3:28][N:29]1[CH2:5][CH2:6][N: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)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 2733832Lithium HexamethyldisilazideHCID 109917693-Bromo-1-(triisopropylsilyl)indoleHCID 589751763-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 589751093-(4-Methyl-piperazin-1-yl)-1-triisopropylsilanyl-1H-indoleYield 32%

Reagents, catalysts & solvents 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylCatalystHCID 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), 1-methyl-piperazine (0.30 g, 3.00 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). Purify by flash chromatography using 0 to 12% of MeOH in dichloromethane to give the title compound (0.23 g, 32%). MS (ES) 372.1 (M+1)+.

Workup

  1. customPurify by flash chromatography

Sources & evidence

ORD record
ord-a1bd44d0cd71424da78b2121dd96c2d7
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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