Triethylamine → HCID 22627647, compound

HRID 1954217Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6](OS(C(F)(F)F)(=O)=O)[C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[CH:4]=1)#[N:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C=O>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Under nitrogen atmosphere, 1.2 g of 2-cyano-7-methoxy-8-trifluoromethanesulfonyloxynaphthalene, 0.66 g of phenylboronic acid, 0.12 g of tetrakis triphenylphosphine palladium and 1.5 ml of triethyl-amine were suspended in 20 ml of anhydrous N,N-dimethylformamide. The resulting suspension was stirred under heating at 100° C. for 1.5 hours and cooled to room temperature by allowing to stand. A saturated aqueous solution of ammonium chloride was added to the resulting reaction mixture, followed by the extraction with ethyl acetate (50 ml×2). The organic layers were combined, washed with brine, died over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the resulting crude product was purified by silica gel column chromatography to give 0.95 g of the title compound.

Workup

temperaturecooled to room temperature
extractionfollowed by the extraction with ethyl acetate (50 ml×2)
washwashed with brine
filtrationfiltered
concentrationThe filtrate was concentrated
customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e494d8d10f0e4ab48a0d5fb2f0e3e253
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121309

Reaction notes

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