Propargyl alcohol → HCID 59232565, compound

HRID 659965Notes

Reaction equation

HRID 659965 reaction equation
[N:1]1([NH:7][C:8]([C:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:31]([OH:34])[C:32]#[CH:33].[Cl-].[NH4+]>N1CCCC1.[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>[N:1]1([NH:7][C:8]([C:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:33]#[C:32][CH2:31][OH:34])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 25517Ammonium ChlorideHCID 10413921HCID 10413921, compound

Product 1

HCID 59232565HCID 59232565, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 31268PyrrolidineSolvent2×

Procedure

To a stirred solution of 5-(4-Bromo-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (40 mg, 0.078 mmol) in pyrrolidine (2.5 ml) was added a catalytic amount of tetrakis (triphenylphosphine) palladium under an atmosphere of Argon. After stirring the contents for 5 min at room temperature, a solution of propargyl alcohol (10 mg, 0.178 m mol) in pyrrolidine (1.5 ml) was added to the reaction mixture. The contents were heated at 80-85° C. for 10 h. Then a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic extract was dried over MgSO4 and the solvent was removed in vacuo. Purification by flash column chromatography on silica gel (petroleum ether-ethyl acetate, 7:3) afforded 28 mg (74%) of 2-1 as white solid.

Workup

  1. temperatureThe contents were heated at 80-85° C. for 10 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customPurification by flash column chromatography on silica gel (petroleum ether-ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-be85210fe35643b7aa4d811d7975bb85
Source dataset
uspto-grants-2011_12
Patent number
US08084451B2

Reaction notes

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