Hexane → HCID 68930450, compound

HRID 1027469Notes

Reaction equation

HRID 1027469 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:11]([CH3:23])[CH2:10]2)=[CH:4][CH:3]=1.[C:30]1([C:36]#[CH:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC.CCOC(C)=O>[CH3:23][C@@H:11]1[CH2:10][N:9]([C@@H:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[CH:6]=[CH:7][C:2]([C:37]#[C:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:3][CH:4]=2)[CH2:14][CH2:13][N:12]1[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 8058HexaneHCID 10821PhenylacetyleneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 68929842HCID 68929842, compound

Product 1

HCID 68930450HCID 68930450, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 2-((R)-4-((S)-(4-bromophenyl)(phenyl)methyl)-2-methyl-piperazin-1-yl)acetate (459 mg, 0.1 mmol, its preparation follows the general procedures of Reference G), 1-phenylethyne (0.137 ml, 1.249 mmol), tetrabutylammonium fluoride trihydrate (946 mg, 2.997 mmol) and dichlorobis(triphenylphosphine)palladium(ii) (21.0 mg, 0.030 mmol) was heated at 80° C. under N2 atmosphere for 1 h. The residue was subjected to flash chromatography (SiO2, hexane to hexane/EtOAc=100:10 to 100:15 to 100:20) to give tert-butyl 2-((R)-2-methyl-4-((S)-phenyl(4-(2-phenylethynyl)phenyl)methyl)-piperazin-1-yl)acetate (460 mg) as a yellow oil.

Workup

  1. custom459 mg, 0.1 mmol, its preparation

Sources & evidence

ORD record
ord-8a045d832aa34a7dbebd48c6917f3ad5
Source dataset
uspto-grants-2014_05
Patent number
US08735383B2

Reaction notes

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