2-Methylpiperazine → 6-(3-Methylpiperazinyl)-1-triisopropylsilyl-indole

HRID 2084059Notes

Reaction equation

HRID 2084059 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.[CH3:21][CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]1.CC([O-])(C)C.[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C1(C)C(C)=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:21][CH:22]1[NH:23][CH2:24][CH2:25][N:26]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=2)[CH2:27]1

Participants

7

Reactant 4

HCID 660572-MethylpiperazineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 129912436-bromo-1-(triisopropylsilyl)-1H-indoleHCID 23676156Sodium t-butoxide

Product 1

HCID 103392136-(3-Methylpiperazinyl)-1-triisopropylsilyl-indole

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

From 6-Bromo-1-triisopropylsilyl-indole (400 mg, 1.14 mmol), 2-methylpiperazine (1.36 mg, 13.6 mmol), NaOtBu (0.153 mg, 1.59 mmol), tBu3P (12 mg) and Pd(OAc)2 (3 mg) in xylene (1 ml) under argon. The reaction mixture was heated to 120° C. (59%).

Sources & evidence

ORD record
ord-d180ad88bc724dbfa90aacf8be0f1e03
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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