Trimethylsilyl iodide → HCID 68737441, compound

HRID 870006Notes

Reaction equation

HRID 870006 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20]([C:22]5[CH:23]=[N:24][C:25]([O:28]C)=[CH:26][CH:27]=5)[CH:19]=[C:18]([CH3:30])[CH:17]=4)=[O:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Si](I)(C)(C)C>CO>[O:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]([CH3:30])[CH:19]=[C:20]([C:22]5[CH:27]=[CH:26][C:25](=[O:28])[NH:24][CH:23]=5)[N:21]=4)=[O:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68722356HCID 68722356, compound

Product 1

HCID 68737441HCID 68737441, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a slurry of 1-(2,3-dihydrobenzofuran-6-yl)-N-(6′-methoxy-4-methyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (20 mg, 0.049 mmol) in acetonitrilee (1.5 mL) was added TMS-I (28.4 μL, 0.19 mmol) and the mixture was stirred at 55° C. for 7 h. The reaction was diluted with methanol (1.0 mL) and stirred at room temperature for 2 h. The resulting mixture was concentrated under vacuum, and taken into ethyl acetate (10 mL). The organic solution was washed with sodium bisulphate (2×2 ml), water (2×3 mL), dried over sodium sulphate and concentrated under vacuum. The solid was stirred with methanol (1.0 mL) at 40° C. for 10 min and collected by filtration, washed with methanol (1.0 mL) and dried under vacuum to yield the product (8.0 mg, 41%). ESI-MS m/z calc. 387.4. found 388.2 (M+1)+. Retention time 1.44 minutes.

Workup

  1. stirringstirred at room temperature for 2 h
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. washThe organic solution was washed with sodium bisulphate (2×2 ml), water (2×3 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. stirringThe solid was stirred with methanol (1.0 mL) at 40° C. for 10 min
  7. filtrationcollected by filtration
  8. washwashed with methanol (1.0 mL)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-c1122fd219de4abdb7baa086574c7141
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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