Toluene → HCID 57849603, compound

HRID 737088Notes

Reaction equation

HRID 737088 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH:11]([CH3:13])[O:10][CH:9]([CH3:14])[CH2:8]2)=[CH:4][CH:3]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH3:14][CH:9]1[O:10][CH:11]([CH3:13])[CH2:12][N:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18]([F:29])([F:28])[F:17])=[CH:3][CH:4]=2)[CH2:8]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 5332987HCID 5332987, compound

Product 1

HCID 57849603HCID 57849603, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

100 mg of 4-(4-Bromo-benzyl)-2,6-dimethyl-morpholine was combined with 100 mg of 2-(Trifluoromethyl)phenyl boronic acid, 20 mg of tetrakis(triphenylphosphine)palladium(0), 1.179 mL of 2M sodium carbonate solution, 3.2 mL toluene and 1.6 mL ethanol. The reaction mixture was heated in a sealed tube at 120° C. overnight in an oil bath. The reaction mixture was filtered through Celite and concentrated in vacuo. The residue was purified by reverse phase HPLC. ES MS (+) m/z 350.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-dc10748d62664061ad0a7713171c1f66
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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