((1,1-Dimethyl-2-propynyl)oxy)trimethylsilane → HCID 131736032, compound

HRID 1049578Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([O:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]=[CH:9][C:8]=1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[F:29])(=O)=O.[CH3:32][Si:33]([CH3:41])([CH3:40])[O:34][C:35]([CH3:39])([C:37]#[CH:38])[CH3:36]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I.C(N(CC)CC)C>[C:14](=[O:15])([O:13][C:11]1[CH:12]=[CH:7][C:8]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=2[F:29])=[C:9]([C:38]#[C:37][C:35]([CH3:39])([O:34][Si:33]([CH3:41])([CH3:40])[CH3:32])[CH3:36])[CH:10]=1)[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

Under a nitrogen atmosphere, to a mixture of 4-((tert-butoxycarbonyl)oxy)-2′-fluoro-5′-methoxybiphenyl-2-yl trifluoromethanesulfonate (408 mg), tetrakis(triphenylphosphine)palladium (308 mg), copper iodide (32 mg) and triethylamine (10 mL) was added trimethyl((2-methylbut-3-yn-2-yl)oxy)silane (1.7 mL). The mixture was stirred at 80° C. for 15 hr, and tetrakis(triphenylphosphine)palladium (308 mg) was added. The mixture was stirred at 80° C. for 20 hr, 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 (232 mg) as a yellow oil.

Workup

stirringThe mixture was stirred at 80° C. for 20 hr
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b0c98111ffd843d081cf327cb53162ba
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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