Cesium carbonate → HCID 90052195, compound

HRID 2284807Notes

Reaction equation

HRID 2284807 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:16][CH2:17][CH3:18])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(OCC)(=O)C>[C:30]([C:29]1[CH:32]=[CH:33][C:26]([NH:25][C:2]2[CH:7]=[C:6]([N:8]([CH2:16][CH2:17][CH3:18])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:4][N:3]=2)=[CH:27][CH:28]=1)#[N:31]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 133964-AminobenzonitrileHCID 312751,4-DioxaneHCID 90051680HCID 90051680, compound

Product 1

HCID 90052195HCID 90052195, compoundYield 15.7%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To tert-butyl (2-chloro-5-(5-hydroxy-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate (S10, 88 mg), 4-aminobenzonitrile (59 mg), tris(dibenzylideneacetone)dipalladium(0) (22 mg), 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (29 mg) and cesium carbonate (203 mg), 1,4-dioxane (2.5 mL) was added at room temperature, and the mixture was stirred at 100° C. for 10 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The insoluble matter was removed by filtration through Cerite. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent, 100 to 30% hexane in ethyl acetate) to obtain tert-butyl (2-((4-cyanophenyl)amino)-5-(5-hydroxy-1-pentyn-1-yl)pyridin-4-yl)(propyl)carbamate (S11, 17 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble matter was removed by filtration through Cerite
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (eluent, 100 to 30% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-e73428a384f440b1b5fcd399093df536
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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