Sodium Iodide → (2E)-2-[(3-iodo-4-pyridyl)methylene]-6-methoxy-tetralin-1-one

HRID 2207188Notes

Reaction equation

CNC1CCCCC1NC.O1CCOCC1.Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1/[CH:24]=[C:25]1/[C:26](=[O:37])[C:27]2[C:32]([CH2:33][CH2:34]/1)=[CH:31][C:30]([O:35][CH3:36])=[CH:29][CH:28]=2.[Na+].[I-:39]>[Cu]I.O>[I:39][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1/[CH:24]=[C:25]1/[C:26](=[O:37])[C:27]2[C:32]([CH2:33][CH2:34]/1)=[CH:31][C:30]([O:35][CH3:36])=[CH:29][CH:28]=2

Participants

Conditions

Temperature: 110 °C

Procedure

In a Schlenk tube, N,N′-dimethyl-1,2-cyclohexanediamine 85% (32 μL, 0.20 mmol) and dioxane (2 mL) were added to a mixture of CuI (19.2 mg, 0.1 mmol), compound 87 (688 mg, 2.0 mmol) and NaI (600 mg, 4.00 mmol). The Schlenk tube was sealed with a Teflon cap and the reaction mixture was stirred at 110° C. for 24 h. After cooling, the resulting suspension was poured into water (20 mL), and extracted with dichloromethane (3×). The combined organic phases were dried over magnesium sulfate and concentrated to dryness. The product was allowed to crystallize at room temperature. The residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether) to afford the title compound 88 as a yellow solid (Yield 703.8 mg, 90%).

Workup

customcap
temperatureAfter cooling
extractionextracted with dichloromethane (3×)
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated to dryness
customto crystallize at room temperature
customThe residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-651f420f366e48b09f50f77e29eba715
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376387B2

Reaction notes

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