Cesium carbonate → HCID 131728128, compound

HRID 2238663Notes

Reaction equation

HRID 2238663 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[F:18][C:19]([F:29])([F:28])[C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([N:25]2[CH2:26][CH2:27][N:22]([C:20](=[O:21])[C:19]([F:29])([F:18])[F:28])[CH2:23][CH2:24]2)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 7172020TrifluoroacetylpiperazineHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

Product 1

HCID 131728128HCID 131728128, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

The mixture of 100 mg of the t-butyl[(1S)-1-(4-bromophenyl)ethyl]carbamate [106-1], 73 mg of 2,2,2-trifluoro-1-piperazin-1-yl-ethanone (synthesized according to a method disclosed in page 7357-7360 in Tetrahedron Lett. 1995, 41), 3.7 mg of palladium acetate, 10.7 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 217 mg of cesium carbonate, and 3 mL of toluene, was stirred overnight at 100° C. After cooling the reaction mixture back to room temperature, the insolubles were filtered through celite, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by preparative thin-layer chromatography, to obtain 73 mg of t-butyl((1S)-1-{4-[4-(trifluoroacetyl)piperazin-1-yl]phenyl}ethyl)carbamate [110-1] as a white solid.

Workup

  1. customsynthesized
  2. filtrationthe insolubles were filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe thus obtained residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-019a9522a4e5434fb24d949b91108682
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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