Triethylamine → 5-[4-(5-Chloropent-1-yn-1-yl)-2-methoxyphenyl]-2-methyl-1,3-oxazole

HRID 71210

반응식

HRID 71210 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1.[Cl:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:21].C(N(CC)CC)C>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 843081-Pentyne, 5-chloro-HCID 666087325-(4-Bromo-2-methoxyphenyl)-2-methyloxazole

생성물 1

HCID 666082675-[4-(5-Chloropent-1-yn-1-yl)-2-methoxyphenyl]-2-methyl-1,3-oxazole

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A mixture of 5-(4-bromo-2-methoxyphenyl)-2-methyl-1,3-oxazole (6.00 g), 5-chloropent-1-yne (4.74 mL), dichlorobis(triphenylphosphine)palladium(II) (1.57 g), copper(I) iodide (426 mg) and triethylamine (60 mL) was stirred at 70° C. for 3 hr, and diluted with ethyl acetate, and the mixture was filtered through celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.85 g).

후처리

  1. filtrationthe mixture was filtered through celite
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-4cc6270886fc4692977c650aa62d336b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822699B2

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