Toluene → Ammonia

HRID 2182263Notes

Reaction equation

HRID 2182263 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>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>[NH3:4].[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:18]2[CH2:19][CH2:20][CH2:21][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:16][CH2:17]2)[CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 122863-BromopyridineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 108024941-(Pyridin-3-yl)-4-tert-butoxycarbonylhomopiperazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromopyridine (3.95 g, 25.0 mmol), 1-tert-butoxycarbonylhomopiperazine (5.0 g, 25.0 mmol), tetrakis(triphenylphosphine)palladium(0) (145 mg, 0.125 mmol), potassium tert-butoxide (6.1 g, 50.0 mmol) and anhydrous toluene (75 ml) was stirred at 80° C. for 4 h. Water (100 ml) was added and the mixture was extracted three times with ethyl acetate (50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 0.92 g, 13%.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-437a31afd4fc4d398dbcb2ec4b63e7bb
Source dataset
uspto-grants-2005_05
Patent number
US06897219B2

Reaction notes

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