Hydrochloric Acid → HCID 68887805、化合物

HRID 1760581ノート

反応式

HRID 1760581 の反応式
[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]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 110305002-tert-Butyldimethylsiloxybut-3-yneHCID 68890345HCID 68890345、化合物

生成物 1

HCID 68887805HCID 68887805、化合物収率 138.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3e55da47160d40ba9068af211eb8ebd9
出典データセット
uspto-grants-2005_01
特許番号
US06844345B2

反応ノート

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