Hexane → HCID 22462434, compound

HRID 1937020Notes

Reaction equation

HRID 1937020 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li]CCCC.CCCCCC.Br[C:22]1[CH:23]=[CH:24][C:25]2[C:26]3[CH2:35][CH2:34][CH2:33][C:27]=3[C:28](=[O:32])[NH:29][C:30]=2[CH:31]=1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd](Cl)Cl>[N:36]1([C:22]2[CH:23]=[CH:24][C:25]3[C:26]4[CH2:35][CH2:34][CH2:33][C:27]=4[C:28](=[O:32])[NH:29][C:30]=3[CH:31]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

10

Reactant 6

HCID 8058HexaneHCID 8083MorpholineHCID 13838HexamethyldisilazaneHCID 80271Tri-o-tolylphosphineHCID 15429321HCID 15429321, compoundHCID 178418339Butyllithium

Product 1

HCID 22462434HCID 22462434, compoundYield 86.6%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,1,1,3,3,3-hexamethyldisilazane (2.6 ml, 12.5 mmol) in toluene (100 ml) is mixed at 0° C. with 1.6 M of n-BuLi in hexane (7.5 ml, 12.0 mmol) and stirred for 15 minutes at 0° C. 7-Bromo-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one (1.34 g, 5.0 mmol), morpholine (0.65 ml, 7.5 mmol), palladium dichloride (44 mg, 0.25 mmol) and tri-o-tolylphosphine (152 mg, 0.5 mmol) are added to it. The batch is refluxed for 5 hours, diluted with ethyl acetate, washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Purification of the residue on silica gel with dichloromethane-ethanol yields 1.17 g of product.

Workup

  1. temperatureThe batch is refluxed for 5 hours
  2. washwashed with saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum
  5. customPurification of the residue on silica gel with dichloromethane-ethanol

Sources & evidence

ORD record
ord-0d228a2421e640a2abed2d6466c99749
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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