Cesium carbonate → HCID 11352447, compound

HRID 389975Notes

Reaction equation

HRID 389975 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:53]1([CH2:59][CH2:60][CH2:61][NH:62][C:63]([C:65]2[N:70]=[CH:69][C:68](OS(C(F)(F)F)(=O)=O)=[CH:67][CH:66]=2)=[O:64])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[N:79]1([C:85]([C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][C:88]=2[C:93]([F:96])([F:95])[F:94])=[O:86])[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]1>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:53]1([CH2:59][CH2:60][CH2:61][NH:62][C:63]([C:65]2[CH:66]=[CH:67][C:68]([N:82]3[CH2:83][CH2:84][N:79]([C:85](=[O:86])[C:87]4[CH:92]=[CH:91][CH:90]=[CH:89][C:88]=4[C:93]([F:96])([F:94])[F:95])[CH2:80][CH2:81]3)=[CH:69][N:70]=2)=[O:64])[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazineHCID 86609725Trifluoromethanesulfonic acid 6-(3-phenylpropylcarbamoyl)pyridin-3-yl ester

Product 1

HCID 11352447HCID 11352447, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

A 50-mL flask was charged with cesium carbonate (0.078 g, 0.238 mmol), palladium diacetate (0.0019 g, 0.0085 mmol) and BINAP (0.0079 g, 0.013 mmol) and flushed with argon for 30 minutes. A solution of trifluoromethanesulfonic acid 6-(3-phenylpropylcarbamoyl)pyridin-3-yl ester (0.066 g, 0.17 mmol) and piperazin-1-yl-(2-trifluoromethylphenyl)methanone (0.053 g, 0.20 mmol) in toluene (2 mL) was added via syringe. The reaction mixture was heated at 100 C for 26 h, cooled to room temperature, diluted with toluene (20 mL), filtered and concentrated in vacuo. The crude product was purified by column chromatography to afford the title compound as a white solid (0.011 g, 13% yield). 1H NMR (300 MHz, CDCl3) δ 8.15, 8.04, 7.85, 7.74, 7.50-7.65, 7.36, 7.30-7.10, 3.90-4.10, 3.55-3.30, 3.22, 2.72, 1.96. MS (ES+) m/z 497.4 (M+1).

Workup

  1. customflushed with argon for 30 minutes
  2. temperatureThe reaction mixture was heated at 100 C for 26 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c3ccdbbd40eb419396433ed3049bfb37
Source dataset
uspto-grants-2013_02
Patent number
US08383628B2

Reaction notes

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