Trimethylsilyl iodide → HCID 25117653, compound

HRID 870011Notes

Reaction equation

HRID 870011 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20]([C:22]5[CH:23]=[N:24][C:25]([O:29]C)=[C:26]([CH3:28])[CH:27]=5)[C:19]([CH3:31])=[CH:18][CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH2:3][O:2]1.[Si](I)(C)(C)C>C(#N)C.C(Cl)Cl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:31])=[C:20]([C:22]5[CH:27]=[C:26]([CH3:28])[C:25](=[O:29])[NH:24][CH:23]=5)[N:21]=4)=[O:14])[CH2:11][CH2:12]3)=[CH:7][CH:8]=2)[CH2:3][O:2]1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 687244141-(1,3-Dihydroisobenzofuran-5-yl)-N-(6'-methoxy-3,5'-dimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

Product 1

HCID 25117653HCID 25117653, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(1,3-dihydroisobenzofuran-5-yl)-N-(6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (40 mg, 0.1 mmol) in acetonitrile (2 mL) was added TMS-Iodide (54.8 μL, 0.39 mmol). The reaction was stirred at 50° C. for 20 min. The reaction solution was diluted with CH2Cl2 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/water). ESI-MS m/z calc. 401.1. found 402.5 (M+1)+. Retention time 1.29 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/water)

Sources & evidence

ORD record
ord-c258e717ccfa402b86118f512c70d1a8
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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