Potassium Carbonate → HCID 11582863, compound

HRID 1783369Notes

Reaction equation

HRID 1783369 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:13]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:12][C:11]=2Br)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:13]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:12][C:11]=2[C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11640647HCID 11640647, compound

Product 1

HCID 11582863HCID 11582863, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolvent

Conditions

Temperature
130 °C

Procedure

2-Cyclopentyl-N-(2-bromo-6-trifluoromethyl-4-morpholin-4-yl-phenyl)-acetamide (1b, 15 mg), 3-pyridylboronic acid (21 mg), aqueous potassium carbonate (5 M, 90 μL) and palladium(II) acetate (1 mg) were mixed in acetone (2 mL) and heated to 130° C. for 20 minutes in a sealed microwave process vial. The reaction mixture was filtered through silica (500 mg), concentrated in vacuo, redissolved in dimethyl sulfoxide (0.5 mL) and subjected to preparative LC-MS purification to furnish 2.7 mg (18% yield) of the title compound as a colorless oil. LC-MS (m/z) 434 (MH+); tR=1.89, (UV, ELSD) 99%,99%.

Workup

  1. filtrationThe reaction mixture was filtered through silica (500 mg)
  2. concentrationconcentrated in vacuo
  3. dissolutionredissolved in dimethyl sulfoxide (0.5 mL)
  4. customsubjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-ece7f9c6febb462db1b38004d1cc89cf
Source dataset
uspto-grants-2009_03
Patent number
US07501414B2

Reaction notes

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