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

HRID 869996Notes

Reaction equation

HRID 869996 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20]([C:22]5[C:23]([O:29]C)=[N:24][CH:25]=[C:26]([CH3:28])[CH:27]=5)[C:19]([CH3:31])=[CH:18][CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.I[Si](C)(C)C>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:31])=[C:20]([C:22]5[C:23](=[O:29])[NH:24][CH:25]=[C:26]([CH3:28])[CH:27]=5)[N:21]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 687233571-(2,3-Dihydrobenzofuran-5-yl)-n-(2'-methoxy-3,5'-dimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

Product 1

HCID 687405121-(2,3-Dihydrobenzofuran-5-yl)-n-(5-methyl-6-(5-methyl-2-oxo-1,2-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-(2,3-dihydrobenzofuran-5-yl)-N-(2′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (90 mg, 0.2 mmol) in acetonitrile (4 mL) at 50° C. was added iodotrimethylsilane (87 mg, 0.4 mmol). The reaction was heated for one hour before being quenched with methanol (1 mL). The reaction was diluted with dichloromethane (15 mL) and washed with an aqueous saturated sodium bisulfite solution (2×15 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting white solid was purified by silica gel chromatography (eluting with 0-10% methanol in ethyl acetate) to yield the product (49 mg, 55%) as a white solid. ESI-MS m/z calc. 401.46. found 402.5 (M+1)+. Retention time 1.32 minutes.

Workup

  1. temperatureThe reaction was heated for one hour
  2. custombefore being quenched with methanol (1 mL)
  3. additionThe reaction was diluted with dichloromethane (15 mL)
  4. washwashed with an aqueous saturated sodium bisulfite solution (2×15 mL)
  5. dry with materialThe organics were dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe resulting white solid was purified by silica gel chromatography (eluting with 0-10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-0cacaa3dac144fe89d8dcd181dc51997
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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