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Sodium hydride → tert-Butyl 2-(6-nitro-1H-indol-1-yl)acetate

HRID 453859
Notes
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Reaction equation

HRID 453859 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[Cl-].[NH4+]>CN(C=O)C>[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][N:12]2[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:7]=1)([O-:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 785026-Nitro-1H-indoleHCID 79177tert-Butyl bromoacetate

Product 1

HCID 68498176tert-Butyl 2-(6-nitro-1H-indol-1-yl)acetateYield 47%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

NaH (4.5 mmol, 1.5 equiv.) was suspended in DMF (5 ml), and 6-nitro-indole (3 mmol, 1 equiv.), dissolved in DMF (5 ml), was added at 0° C. The mixture was stirred for 30 min. Then tert-butyl bromoacetate (3.6 mmol, 1.2 equiv.) was added and the mixture was stirred for 15 h at 25° C. The reaction mixture was hydrolysed with ammonium chloride and extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 20 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography. Yield: 47%

Workup

  1. additionwas added at 0° C
  2. stirringthe mixture was stirred for 15 h at 25° C
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 20 ml),
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-72655f08ffef4a4cafbdce7b6f6bacb6
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492559B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes