Dimethylformamide → HCID 86693803, compound

HRID 1754881Notes

Reaction equation

CN(C)C=O.C(N(CC)CC)C.[C:13]([C:17]#[CH:18])([CH3:16])([CH3:15])[CH3:14].[CH2:19]([N:21]([CH3:32])[CH:22]=[N:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][C:25]=1[CH3:31])[CH3:20]>[Cu](I)I.C(OCC)(=O)C.O>[CH2:19]([N:21]([CH3:32])[CH:22]=[N:23][C:24]1[CH:29]=[CH:28][C:27]([C:18]#[C:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:26][C:25]=1[CH3:31])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

Dimethylformamide (10 ml), 10 ml of triethylamine, 0.27 g of tert-butylacetylene, 0.11 g of palladium chloride-ditriphenylphosphine complex, and 0.03 g of copper iodide were added to 0.50 g of the N-ethyl-N-methyl-N′-(4-iodo-2-methylphenyl)formamidine (Compound 2-2) produced in Reference Example 2, and the mixture was stirred at 80° C. for 12 hours. After completion of the reaction, water was added to the reaction solution, and extraction was performed 3 times with ethyl acetate. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), thereby obtaining 0.10 g of N-ethyl-N-methyl-N′-[2-methyl-4-(3,3-dimethyl-1-butynyl)phenyl]formamidine (Compound 66).

Workup

customproduced in Reference Example 2
additionwas added to the reaction solution, and extraction
customThe organic layer was collected
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-1039f1e186f34c7c8c6c9f37b1fe0a94
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169276B2

Reaction notes

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