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

HRID 547071

반응식

HRID 547071 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 57443527HCID 57443527, 화합물수율 78.3%

시약·촉매·용매 3

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

반응 조건

온도
160 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a10a42cca6f44efcb0c862343fb0636b
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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