Sodium Carbonate → HCID 11675715, compound

HRID 1445801Notes

Reaction equation

HRID 1445801 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:27][C:28]([F:39])([F:38])[C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1>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>[CH3:20][C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([C:28]([F:39])([F:38])[F:27])[CH:34]=3)=[CH:3][CH:4]=2)=[N:12][C:11]=1[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 116815462-(4-Bromo-phenyl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole

Product 1

HCID 11675715HCID 11675715, compoundYield 65%

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-pyrrolidin-1-yl-ethyl)-oxazole (100 mg, 0.299 mmol), sodium carbonate (94.9 mg, 0.895 mmol) and 3-Trifluoromethylbenzene boronic acid (284 mg, 1.49 mmol) in toluene (5 mL), water (1 mL) and ethanol (1.5 mL) under nitrogen was added Tetrakis(triphenylphosphine) palladium (0) (34.5 mg, 0.030 mmol). The reaction was then heated to reflux for 48 h. The reaction was allowed to cool and bound to a SCX-2 cartridge (5 g). The cartridge was washed with one cartridge volume of dimethylformamide and two volumes of methanol. The product was eluted using 2M ammonia in methanol. The ammonia/methanol solution was evaporated on a Genevac® HT4. The sample was further purified by prep-LCMS. The resulting acetonitrile/water fractions were combined and evaporated using a Genevac® HT4 to give 77.7 mg of a colourless oil (65%). MS (m/e): 401.2 (M+1)

Workup

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

Sources & evidence

ORD record
ord-5f895611321242b4aeaac2f37dc74b66
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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