Sodium Iodide → HCID 18381962, compound

HRID 751516Notes

Reaction equation

HRID 751516 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH:30](O)[C:31]([NH2:33])=[O:32])=[CH:22]2)[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH2:30][C:31]([NH2:33])=[O:32])=[CH:22]2)[CH2:17][CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 69269014HCID 69269014, compound

Product 1

HCID 18381962HCID 18381962, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve trimethylsilyl chloride (2.1 mL, 6 eq) and sodium iodide (2.5 g, 6 eq) in acetronitrile (15 mL) and cool to 0° C. while under nitrogen. Dissolve 2-[1-(1-benzylpiperidin-4-yl)-1H-indol-3-yl]-2-hydroxyacetamide (1.0 g, 2.75 mmol) in acetonitrile (10 mL) and add dropwise to the reaction. Let stir overnight and gradually warm to room temperature. Extract with 5% NaHSO3 against ethyl acetate then wash with brine. Basify aqueous layer with saturated sodium bicarbonate and wash with ethyl acetate once more. Combine organic layers and dry over magnesium sulfate. Filter and concentrate. Triturate from hot diethyl ether to afford product (0.64 g, 67%) as a white solid. MS (ES, m/z): 348.0 (M+1).

Workup

  1. temperaturegradually warm to room temperature
  2. extractionExtract with 5% NaHSO3 against ethyl acetate
  3. washthen wash with brine
  4. washBasify aqueous layer with saturated sodium bicarbonate and wash with ethyl acetate once more
  5. dry with materialCombine organic layers and dry over magnesium sulfate
  6. filtrationFilter
  7. concentrationconcentrate
  8. customTriturate from hot diethyl ether

Sources & evidence

ORD record
ord-c8482bd0d6ea4bf894dbcfb07c78d42b
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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