Hydrochloric Acid → HCID 68887805, compound

HRID 1760581Notes

Reaction equation

HRID 1760581 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 68887805HCID 68887805, compoundYield 138.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3e55da47160d40ba9068af211eb8ebd9
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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