Toluene → HCID 57849631, compound

HRID 737083Notes

Reaction equation

HRID 737083 reaction equation
Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[C:34]1(C)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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>[C:34]1([CH:7]2[O:8][CH2:9][CH2:10][N:5]([CH2:4][C:3]3[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=3[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]([F:27])([F:26])[F:15])[CH2:6]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 28454774-(2-Bromobenzyl)morpholine

Product 1

HCID 57849631HCID 57849631, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

100 mg of 4-(2-Bromo-benzyl)-morpholine was combined with 86 mg of 2-(Trifluoromethyl)phenyl boronic acid, 17 mg of tetrakis(triphenylphosphine)palladium(0), 1.0 mL of 2M sodium carbonate solution, 2.71 mL toluene and 1.4 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 flash chromatography using flash chromatography using an ethyl acetate/hexanes gradient. 74 mg of product is obtained. ES MS (+) m/z 398

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6f9bfe411bf7419e92ec1efd1c10d0fd
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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