Water → HCID 69997151, 화합물

HRID 963430노트

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HRID 963430 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:2].C([Si:22]([CH3:25])([CH3:24])[CH3:23])#C.O.[CH2:27](N(CC)CC)[CH3:28]>CN(C)C=O.[Cu]I>[CH2:27]([C:2]#[C:1][N:3]1[C:12]2[C:7](=[CH:8][C:9]([Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:28]

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 619729HCID 619729, 화합물

생성물 1

HCID 69997151HCID 69997151, 화합물수율 80%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of ethyl 1-ethyl-6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 13h)), 1.94 ml of ethynyltrimethylsilane, 70 mg of bis-trimethylphosphine-palladium dichloride and 2.5 mg of copper(I) iodide in 7 ml of triethylamine and 7 ml of dimethylformamide is stirred at 60° for 9 hrs. After cooling to room temperature the reaction mixture is treated with 100 ml of water and extracted twice with 50 ml of methylene chloride each time. The combined organic phases are washed twice with 250 ml of water each time and once with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate. The crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1. 1.27 g (80%) of ethyl 1-ethyl-6-trimethylsilyl-ethynyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate are obtained.

후처리

  1. extractionextracted twice with 50 ml of methylene chloride each time
  2. washThe combined organic phases are washed twice with 250 ml of water each time
  3. dry with materialonce with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate
  4. customThe crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1

출처 및 근거

ORD 기록
ord-b05545c695d14780a152db0bc7a6d2c2
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763450

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