Isobutyl iodide → HCID 69065596, compound

HRID 1817508Notes

Reaction equation

HRID 1817508 reaction equation
[Si:1]([O:18][C:19]1[CH:20]=[C:21]([C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][N:28]=2)=[O:26])[CH:22]=[CH:23][CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:39][CH:40]([CH3:42])[CH3:41].CCCCCC.C(OCC)(=O)C>CN(C=O)C>[C:14]([Si:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:18][C:19]1[CH:20]=[C:21]([C:25]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH2:39][CH:40]([CH3:42])[CH3:41])[N:28]=2)=[O:26])[CH:22]=[CH:23][CH:24]=1)([CH3:16])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 69059931HCID 69059931, compound

Product 1

HCID 69065596HCID 69065596, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3-{[tert-butyl(diphenyl)silyl]oxy}phenyl)(1H-indazol-3-yl)methanone (0.67 g, 0.0014 mol) was dissolved in DMF (10 mL). Sodium hydride (66%, 0.042 g, 0.0017 mol) was added, and the reaction was stirred until gas evolution stops. 1-iodo-2-methylpropane (0.242 mL, 0.0021 mol) was added. The reaction was stirred at room temperature overnight. The reaction is quenched with water and extracted with ethyl acetate. The desired product (0.650 g, 0.0012 mol, 87%) is isolated by chromatography with hexane/ethyl acetate (10:1).

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customThe reaction is quenched with water
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-7e6d3479a19e4267b633bb78f375a57d
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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