Potassium Iodide → HCID 71510469, compound

HRID 2282995Notes

Reaction equation

HRID 2282995 reaction equation
[F:1][CH:2]([F:39])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH2:29][CH:28]([C:30]5[C:35]([F:36])=[CH:34][CH:33]=[C:32]([OH:37])[C:31]=5[F:38])[O:27][N:26]=4)[N:24]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:49][C:50]#[CH:51].[Cl-].[NH4+]>CN(C)C=O.C1(C)C=CC=CC=1>[F:39][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([CH:8]([F:9])[F:10])[N:5]([CH2:11][C:12]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH2:29][CH:28]([C:30]5[C:35]([F:36])=[CH:34][CH:33]=[C:32]([O:37][CH2:51][C:50]#[CH:49])[C:31]=5[F:38])[O:27][N:26]=4)[N:24]=3)[CH2:18][CH2:19]2)=[O:13])[N:4]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 86719954HCID 86719954, compound

Product 1

HCID 71510469HCID 71510469, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2,6-difluoro-3-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (1.82 g) and potassium carbonate (657 mg) in N,N-dimethylformamide (15 ml) are added, at room temperature, potassium iodide (289 mg) and 3-bromoprop-1-yne (755 mg)) (80 wt % in toluene). The reaction mixture is stirred at 80° C. for 4 h. Then the mixture is admixed with saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated. Purification by column chromatography gives 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2,6-difluoro-3-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (1.68 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-0e9bac1723be410aa95fc8440a341ec0
Source dataset
uspto-grants-2015_09
Patent number
US09144238B2

Reaction notes

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