Toluene → HCID 11284391, compound

HRID 747056Notes

Reaction equation

HRID 747056 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C@H:13]([NH:17][C:18](=[O:37])[CH2:19][CH:20]3[C:25](=[O:26])[NH:24][CH2:23][CH2:22][N:21]3[S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.B(O)(O)[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([C:47]([NH2:49])=[O:48])[CH:42]=1.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].CCO>[O:26]=[C:25]1[NH:24][CH2:23][CH2:22][N:21]([S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:20]1[CH2:19][C:18]([NH:17][C@@H:13]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:41]3[CH:42]=[C:43]([CH:44]=[CH:45][CH:46]=3)[C:47]([NH2:49])=[O:48])[CH:16]=[CH:15][C:14]1=2)=[O:37]

Participants

8

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 59747956HCID 59747956, compound

Product 1

HCID 11284391HCID 11284391, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a 25 mL pressure tube was added (R)-5-(2-(3-oxo-1-tosylpiperazin-2-yl)acetamido)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (150 mg, 0.25 mmol), benzamide-3-boronic acid (Frontier, 63 mg, 0.38 mmol), tetrakis(triphenylphosphine)-palladium (O) (Aldrich, 30 mg, 0.025 mmol), Toluene (1.5 mL), EtOH (0.4 μL), and 1M NaHCO3 (0.4 mL) at room temperature under N2. The reaction mixture was sealed and stirred at 80° C. overnight, cooled to room temperature, and diluted with EtOAc (40 mL). The organic layer was separated, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to provide the title compound. MS (ES1): 561 (M+H)+.

Workup

  1. customThe reaction mixture was sealed
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. washwashed with saturated NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f708488dd3934593a19129f52f0a3751
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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