Toluene → HCID 67361124, compound

HRID 1909093

Reaction equation

HRID 1909093 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8]2([CH3:15])[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]2)=[CH:4][CH:3]=1.[F:18][C:19]([F:35])([F:34])[O:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:23][CH:22]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O.C(OCC)(=O)C>[F:35][C:19]([F:18])([F:34])[O:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH:26]2[CH2:27][CH2:28][N:29]([C:2]3[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8]4([CH3:15])[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]4)=[CH:4][CH:3]=3)[CH2:30][CH2:31]2)=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidineHCID 23676156Sodium t-butoxideHCID 710593314-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane

Product 1

HCID 67361124HCID 67361124, compoundYield 93.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 86674235Tri-tert-butylphosphine tetraphenylborateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane (156 mg, 0.518 mmol), 4-[4-(trifluoromethoxy)phenoxy]piperidine (135 mg, 0.517 mmol), palladium acetate (1.2 mg, 0.0053 mmol), tri-tert-butylphosphine tetraphenylborate (2.7 mg, 0.0052 mmol), sodium tert-butoxide (55 mg, 0.57 mmol), and toluene (2 mL) were mixed and stirred under reflux for 2 hours. Ethyl acetate and water were added to the reaction mixture, followed by extraction. The organic layer was washed with water twice. A residue was obtained by concentrating the organic layer under reduced pressure, and the resulting residue was then subjected to chromatography refining (methylene chloride) using silica gel, obtaining 232 mg of the objective compound (yield: 93%).

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionfollowed by extraction
  3. washThe organic layer was washed with water twice
  4. customA residue was obtained
  5. concentrationby concentrating the organic layer under reduced pressure

Sources & evidence

ORD record
ord-d3bee796665b41afb7076e2b8902854f
Source dataset
uspto-grants-2013_12
Patent number
US08598358B2

Linked notes

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