Potassium Iodide → 2-(4-{2-[4-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidin-1-yl)-N,N-dimethylacetamide

HRID 522290Notes

Reaction equation

HRID 522290 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12].Cl.[CH3:17][N:18]1[C:22]2[N:23]=[C:24]([C:46]#[N:47])[N:25]=[C:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[C:29]([C:42]([F:45])([F:44])[F:43])[CH:28]=3)[C:21]=2[CH:20]=[CH:19]1>C(#N)C.O>[C:46]([C:24]1[N:25]=[C:26]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH:36]3[CH2:37][CH2:38][N:39]([CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:40][CH2:41]3)=[C:29]([C:42]([F:43])([F:44])[F:45])[CH:28]=2)[C:21]2[CH:20]=[CH:19][N:18]([CH3:17])[C:22]=2[N:23]=1)#[N:47]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 1178996297-methyl-4-{4-[2-(piperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile monohydrochloride

Product 1

HCID 1178995802-(4-{2-[4-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidin-1-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (133 mg), potassium iodide (160 mg), and 2-chloro-N,N-dimethylacetamide (34 μL) were added to a suspension of 7-methyl-4-{4-[2-(piperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile monohydrochloride (150 mg) in acetonitrile (6 mL) at room temperature, and the mixture was stirred at 60° C. for 2 hours. After the reaction mixture was cooled to room temperature, water was added thereto, extraction thereof was performed using EtOAc, and the extract was washed with a saturated aqueous ammonium chloride solution, water, and saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (Hex:EtOAc=1:3). The obtained product was washed with diisopropyl ether, and collected by filtration, whereby 2-(4-{2-[4-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidin-1-yl)-N,N-dimethylacetamide (118 mg) was obtained as a white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washthe extract was washed with a saturated aqueous ammonium chloride solution, water, and saturated brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (Hex:EtOAc=1:3)
  8. washThe obtained product was washed with diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a13765b223204013a24f95600d875d43
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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