1,2-Dimethoxyethane → 1-(6-Phenyl-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine

HRID 2416610Notes

Reaction equation

HRID 2416610 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.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.COCCOC.C(=O)([O-])[O-].[K+].[K+]>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>[C: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)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 22478562Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 224784591-(6-Phenyl-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

1-(6-Bromo-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine (0.89 g, 2.5 mmol), phenyl boronic acid (0.37 g, 3.0 mmol), tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.12 mmol), 1.2-dimethoxyethane (50 ml), potassium carbonate (1.0 g, 7.5 mmol) and water (7.5 ml) was stirred at reflux overnight. Water (50 ml) was added and the mixture was extracted twice with ethyl acetate (40 ml). Chromatography on silica gel with a mixture of petroleum:ethyl acetate (1:1) gave the title compound as an oil. Yield 0.83 g. 94%.

Workup

  1. temperatureat reflux overnight
  2. extractionthe mixture was extracted twice with ethyl acetate (40 ml)
  3. additionChromatography on silica gel with a mixture of petroleum:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-03bec82529be40b79ed1d2a0ebfb9145
Source dataset
uspto-grants-2004_11
Patent number
US06825189B1

Reaction notes

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