Hydrochloric Acid → HCID 68887805, 화합물

HRID 1760581노트

반응식

HRID 1760581 반응식
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([F:15])=[CH:7][C:6]=1I.[C:18]([Si:22]([CH3:29])([CH3:28])[O:23][CH:24]([CH3:27])[C:25]#[CH:26])([CH3:21])([CH3:20])[CH3:19].O=O.Cl>C(N(CC)CC)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>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([F:15])=[CH:7][C:6]=1[C:26]#[C:25][CH:24]([O:23][Si:22]([C:18]([CH3:19])([CH3:21])[CH3:20])([CH3:29])[CH3:28])[CH3:27]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 110305002-tert-Butyldimethylsiloxybut-3-yneHCID 68890345HCID 68890345, 화합물

생성물 1

HCID 68887805HCID 68887805, 화합물수율 138.9%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

The title compound (ISP-MS: m/e=361.2 ([M+])) was produced from (4-fluoro-2-iodo-5-trifluoromethyl-phenyl)-carbamic acid methyl ester as follows: (4-Fluoro-2-iodo-5-trifluoromethyl-phenyl)-carbamic acid methyl ester (1520 mg) was dissolved in triethylamine (20 mL). Bis-(triphenylphosphine)-palladium (II) dichloride (193 mg; 5 mol %), copper (I) iodide (52 mg; 5 mol %) and tert-butyl-dimethyl-(1-methyl-prop-2-ynyloxy)-silane (1.22 g; 1.2 equivalent) were added and the reaction mixture was heated 3 h at 50° C. under exclusion of oxygen. The reaction mixture was poured into chilled aqueous hydrochloric acid (25%) and extracted three times with ethyl acetate. The organic phases were pooled, dried over sodium sulfate and the solvent was removed. The residue was chromatographed on silica gel (eluant: hexane/ethyl acetate 95/5). 2.44 g of the {2-[3-(tert-butyl-dimethyl-silanyloxy)-but-1-ynyl]-4-fluoro-5-trifluoromethyl-phenyl}-carbamic acid methyl ester (quantitative yield) was obtained.

후처리

  1. additionThe reaction mixture was poured
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel (eluant: hexane/ethyl acetate 95/5)

출처 및 근거

ORD 기록
ord-3e55da47160d40ba9068af211eb8ebd9
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844345B2

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