3-Ethyl-1-pentyn-3-ol → HCID 57443527, compound

HRID 547071

Reaction equation

HRID 547071 reaction equation
[CH2:1]([C:3]([OH:8])([CH2:6][CH3:7])[C:4]#[CH:5])[CH3:2].[CH3:9][O:10][C:11](=[O:45])[CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH2:43][CH3:44])([C:28]3[CH:33]=[CH:32][C:31](OS(C(F)(F)F)(=O)=O)=[C:30]([CH3:42])[CH:29]=3)[CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH:18]=1.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[CH3:9][O:10][C:11](=[O:45])[CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH2:43][CH3:44])([C:28]3[CH:33]=[CH:32][C:31]([C:5]#[C:4][C:3]([CH2:6][CH3:7])([OH:8])[CH2:1][CH3:2])=[C:30]([CH3:42])[CH:29]=3)[CH2:26][CH3:27])=[CH:23][CH:24]=2)[CH:18]=1

Participants

7

Reactant 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 516892Sodium BicarbonateHCID 57709113(5-{4-[1-Ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-phenyl}-pyridin-3-yl)-acetic acid methyl ester

Product 1

HCID 57443527HCID 57443527, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
160 °C

Procedure

3-Ethyl-1-pentyn-3-ol (0.024 mL, 0.188 mmol), a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), dichloromethane complex (1:1) (10.6 mg, 0.013 mmol) and copper (I) iodide (2.5 mg, 0.013 mmol) were added to a solution of (5-{4-[1-ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-phenyl}-pyridin-3-yl)-acetic acid methyl ester (Example 144-(2); 67 mg, 0.125 mmol) in triethylamine (2 mL), and the mixture was stirred with microwave heating at 160° C. for three minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give the target compound (48.7 mg, 78%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a10a42cca6f44efcb0c862343fb0636b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Linked notes

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