Trimethylsilyl iodide → HCID 25118015, compound

HRID 870013Notes

Reaction equation

HRID 870013 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[CH:24]=[N:25][C:26]([O:30]C)=[C:27]([CH3:29])[CH:28]=5)[C:20]([CH3:32])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)[CH:9]=[CH:10][C:2]1=2.[Si](I)(C)(C)C>C(#N)C.ClCCl>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([CH3:32])=[C:21]([C:23]5[CH:28]=[C:27]([CH3:29])[C:26](=[O:30])[NH:25][CH:24]=5)[N:22]=4)=[O:15])[CH2:12][CH2:13]3)[CH:9]=[CH:10][C:2]1=2

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 687406131-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-n-(6'-methoxy-3,5'-dimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

Product 1

HCID 25118015HCID 25118015, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (16 mg, 0.037 mmol) in acetonitrile (1 mL) was added TMS-Iodide (21.10 μL, 0.148 mmol). The reaction was stirred at 50° C. for 20 minutes. 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. 417.5. found 418.3 (M+1)+. Retention time 1.40 minutes.

Workup

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

Sources & evidence

ORD record
ord-b98df524d15941edb7ac15539cd9dbff
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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