Cesium carbonate → HCID 11539545, compound

HRID 1820143Notes

Reaction equation

HRID 1820143 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:35][C:36]([F:49])([F:48])[C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[CH2:47][CH2:46][CH2:45][NH:44]2)=[CH:39][CH:38]=1.Br[C:51]1[CH:56]=[C:55]([CH3:57])[C:54]([NH:58][C:59](=[O:66])[CH2:60][CH:61]2[CH2:65][CH2:64][CH2:63][CH2:62]2)=[C:53]([CH3:67])[CH:52]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH:61]1([CH2:60][C:59]([NH:58][C:54]2[C:53]([CH3:67])=[CH:52][C:51]([N:44]3[CH2:45][CH2:46][CH2:47][CH:43]3[C:40]3[CH:41]=[CH:42][C:37]([C:36]([F:35])([F:48])[F:49])=[CH:38][CH:39]=3)=[CH:56][C:55]=2[CH3:57])=[O:66])[CH2:65][CH2:64][CH2:63][CH2:62]1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 37011532-[4-(trifluoromethyl)phenyl]pyrrolidineHCID 11507840N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

Product 1

HCID 11539545HCID 11539545, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Bis(dibenzylideneacetone)palladium (3.6 mg) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (3.7 mg) were mixed in dry toluene (2 mL) under argon for 5 minutes. To this mixture were added cesium carbonate (41 mg), 2-[4-(trifluoromethyl)phenyl]pyrrolidine (15 mg) and N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (1p, 20 mg) and the reaction was heated to 110° C. in a sealed 4 mL vial under argon for 48 hours. Aqueous sodium bicarbonate (5 mL) was added and the mixture was extracted with ethyl acetate (3×3 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by vacuum liquid chromatography to furnish 7.6 mg (27% yield) of the title compound as an oil. LC-MS-TOF (m/z) 445 (MH+); tR=3.91, (UV, ELSD) 98%, 99%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×3 mL)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by vacuum liquid chromatography

Sources & evidence

ORD record
ord-1b4c0f5140f74cbc8eea96a2cacdd4d0
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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