Dimethylformamide → HCID 86693801, compound

HRID 1754880Notes

Reaction equation

CN(C)C=O.C(N(CC)CC)C.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].[CH3:19][N:20]([CH3:31])[CH:21]=[N:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=1[CH3:30]>[Cu](I)I.C(OCC)(=O)C.O>[CH3:19][N:20]([CH3:31])[CH:21]=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:25][C:24]=1[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

Dimethylformamide (10 ml), 10 ml of triethylamine, 0.33 g of trimethylsilyl acetylene, 0.11 g of palladium chloride-ditriphenylphosphine complex, and 0.03 g of copper iodide were added to 0.50 g of the N,N-dimethyl-N′-(4-iodo-2-methylphenyl)formamidine (Compound 2-1) produced in Reference Example 1, 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 0.20 g of N,N-dimethyl-N′-[2-methyl-4-(2-trimethylsilyl-1-ethynyl)phenyl]formamidine (Compound 49).

Workup

customproduced in Reference Example 1
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-034253b209c7462d85c56a28700dd445
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169276B2

Reaction notes

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