Sodium Carbonate → HCID 11625135, compound

HRID 1445788Notes

Reaction equation

HRID 1445788 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:13]=2)=[CH:5][CH:4]=1.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3[O:10][CH:11]=[C:12]([CH2:14][N:15]4[CH2:19][CH2:18][CH2:17][CH2:16]4)[N:13]=3)=[CH:5][CH:4]=2)=[CH:26][CH:25]=1)(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 68705498HCID 68705498, compound

Product 1

HCID 11625135HCID 11625135, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(4-Bromo-phenyl-4-pyrrolidin-1-ylmethyl-oxazole hydrochloride (See Example 2) (0.151 g, 0.439 mmol), 4-methylsulfonylphenylboronic acid (0.132 g, 0.66 mmol), tetrakis-(triphenylphosphine) palladium (0.010 g, 0.009 mmol), aqueous sodium carbonate (2M, 0.88 mL, 1.76 mmol) and 7 mL of dioxane is placed in a 10 mL CEM microwave tube. The tube is placed in a CEM microwave reactor for 30 minutes at 90° C., 25 psi, and 45 watts of power. The mixture is cooled and concentrated to a dark residue which is purified by radial silica gel chromatography (1% 2M NH3 in MeOH/dichloromethane) to give 0.125 g of the titled compound. MS (m/e): 383.1 (M+1)

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated to a dark residue which
  3. customis purified by radial silica gel chromatography (1% 2M NH3 in MeOH/dichloromethane)

Sources & evidence

ORD record
ord-e213308f1cb9485182c87d84c53b0a01
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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