Trimethylsilyl iodide → 1-(3-Chloro-4-methoxyphenyl)-N-(5-methyl-6-(5-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

HRID 870009Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:13]([NH:15][C:16]3[N:21]=[C:20]([C:22]4[CH:23]=[N:24][C:25]([O:29]C)=[C:26]([CH3:28])[CH:27]=4)[C:19]([CH3:31])=[CH:18][CH:17]=3)=[O:14])[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Si](I)(C)(C)C>C(#N)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH3:31])=[C:20]([C:22]4[CH:27]=[C:26]([CH3:28])[C:25](=[O:29])[NH:24][CH:23]=4)[N:21]=3)=[O:14])[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-(3-chloro-4-methoxyphenyl)-N-(6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (44 mg, 0.10 mmol) in acetonitrile (2 mL) was added TMS-Iodide (57.2 μL, 0.40 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 (10-99% CH3CN in water). ESI-MS m/z calc. 423.1. found 424.3 (M+1)+. Retention time 1.52 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 (10-99% CH3CN in water)

Sources & evidence

ORD record: ord-c463b0040f194aadbad560def1b27414
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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