Chlorosuccinimide → HCID 21260606, compound

HRID 634629Notes

Reaction equation

HRID 634629 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Si:9]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[C:32]1[C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C.O>[Si:9]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([Cl:1])=[C:32]1[C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)([C:22]([CH3:24])([CH3:25])[CH3:23])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 21260597HCID 21260597, compound

Product 1

HCID 21260606HCID 21260606, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

N-Chlorosuccinimide (504 mg) was dissolved in an ethanol (9 ml) and water (1 ml) mixture of the 1-[4-(tert-butyldiphenylsilyloxy)butyl]-2-(3-pyridyl)indole (1.99 g) obtained in the same way as in Example 2(1), and the mixture was reacted at room temperature for 4.5 hours. After the reaction, water was added and the mixture was extracted with ethyl acetate, and the organic phase was washed with brine, then dried over magnesium sulfate, then the solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to obtain 1-[4-(tert-butyldiphenylsilyloxy)butyl]-3-chloro-2-(3-pyridyl)indole (1.24 g).

Workup

  1. customobtained in the same way as in Example 2(1)
  2. customthe mixture was reacted at room temperature for 4.5 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb1f5717f63f4d0a947a123c48ea16b2
Source dataset
uspto-grants-2001_02
Patent number
US06184238B2

Reaction notes

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