Sodium Carbonate → HCID 11618006, compound

HRID 1445869Notes

Reaction equation

HRID 1445869 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:21])=[C:11]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][C@H:16]3[CH3:20])[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:28]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)(=[O:30])[CH3:29]>C1(C)C=CC=CC=1.O.C(O)C.[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>[CH3:21][C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:34]3[CH:35]=[CH:36][C:31]([C:28](=[O:30])[CH3:29])=[CH:32][CH:33]=3)=[CH:3][CH:4]=2)=[N:12][C:11]=1[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH3:20]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 11530378HCID 11530378, compound

Product 1

HCID 11618006HCID 11618006, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-(4-Bromo-phenyl)-5-methyl-4-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-oxazole (100 mg, 0.287 munol), sodium carbonate (91 mg, 0.860 mmol) and 4-acetylphenyl boronic acid (235 mg, 1.43 mmol) in toluene (5 mL), water (1 mL) and ethanol (1.5 mL) under nitrogen is added Tetrakis (triphenylphosphine) palladium (0) (33.1 mg, 0.029 mmol). The reaction is heated at reflux for 48 h. The reaction is allowed to cool and bound to a SCX-2 cartridge (10 g). The cartridge is washed with one cartridge volumes of dimethylformamide and two volume of methanol. The product is eluted using 2M ammonia in methanol. The ammonia/methanol solution is evaporated on a Genevac® HT4. The sample is further purified by prep-LCMS. The resulting acetonitrile/water fractions are combined and evaporated using a Genevac® HT4 to give 62 mg of a colourless oil (56%). MS (m/e) 389.2 (M+1)

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 48 h
  3. temperatureto cool
  4. washThe cartridge is washed with one cartridge volumes of dimethylformamide and two volume of methanol
  5. washThe product is eluted
  6. customThe ammonia/methanol solution is evaporated on a Genevac® HT4
  7. customThe sample is further purified by prep-LCMS
  8. customevaporated

Sources & evidence

ORD record
ord-a5cdbd9fdfef4eed92a95e8f55b6ca0e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…