1,2-Dimethoxyethane → 1-[6-(N-Pyrrolidinyl)-3-pyridyl]-4-tert-butoxycarbonyl homopiperazine

HRID 2182273

Reaction equation

HRID 2182273 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CC(C)([O-])C.[K+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:22]1([C:2]2[N:7]=[CH:6][C:5]([N:8]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 31268PyrrolidineHCID 22478562Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 224784571-[6-(N-Pyrrolidinyl)-3-pyridyl]-4-tert-butoxycarbonyl homopiperazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A stirred solution of 1-(6-Bromo-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine (0.71 g, 2.0 mmol), pyrrolidine (2.0 g, 20 mmol), potassium tert-butoxide (0.45 g, 4.0 mmol), tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 mmol) and 1.2-dimethoxyethane was stirred at reflux overnight. Water (40 ml) was added and the mixture was extracted twice with ethyl acetate (20 ml) Chromatography on silica gel with a mixture of petroleum: ethyl acetate (1:1) gave the title compound as free base. Yield 0.21 g, 30%.

Workup

  1. temperatureat reflux overnight
  2. extractionthe mixture was extracted twice with ethyl acetate (20 ml) Chromatography on silica gel with a mixture of petroleum: ethyl acetate (1:1)

Sources & evidence

ORD record
ord-dbbda2a566ed48e284b0973d208317b6
Source dataset
uspto-grants-2005_05
Patent number
US06897219B2

Linked notes

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