Trimethylsilyl iodide → 1-(3-Methoxyphenyl)-N-(5-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

HRID 870015Notes

Reaction equation

C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([NH:16][C:17]([C:19]3([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[CH2:21][CH2:20]3)=[O:18])[N:10]=2)=[CH:5][C:4]=1[CH3:30].[Si](I)(C)(C)C>C(#N)C.ClCCl>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([C:19]2([C:17]([NH:16][C:11]3[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([C:6]4[CH:5]=[C:4]([CH3:30])[C:3](=[O:2])[NH:8][CH:7]=4)[N:10]=3)=[O:18])[CH2:20][CH2:21]2)[CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)-1-(3-methoxyphenyl)cyclopropanecarboxamide (41 mg, 0.10 mmol) in acetonitrile (2 mL) was added TMS-Iodide (28.0 μL, 0.20 mmol). The reaction was stirred at 50° C. for 20 min. The reaction solution was diluted with dichloromethane and washed with saturated NaHSO3 (2×), brine, dried over MgSO4 and concentrated. The crude product was dissolved in DMSO (1 mL) and purified by reverse phase HPLC (Gilson, 10-99% CH3CN in water) to yield the desired product. ESI-MS m/z calc. 389.4. found 390.5 (M+1)+. Retention time 1.41 minutes.

Workup

washwashed with saturated NaHSO3 (2×), brine
dry with materialdried over MgSO4
concentrationconcentrated
dissolutionThe crude product was dissolved in DMSO (1 mL)
custompurified by reverse phase HPLC (Gilson, 10-99% CH3CN in water)

Sources & evidence

ORD record: ord-fdc0193f8b5e4637aa395bc6479b02e0
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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