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Sodium Azide → 3-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole

HRID 1918621
Notes
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Reaction equation

HRID 1918621 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[C:10]([CH3:13])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[C:10]([CH3:13])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])=[N+:23]=[N-:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 668318963-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole

Product 1

HCID 866638373-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indoleYield 105.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole (0.725 g; 1.87 mmol) and sodium azide (0.365 g; 5.62 mmol) in DMF (8 mL) was stirred at 70° C. for 4 hours and concentrated under reduced pressure. The residue was diluted in ethyl acetate, washed with brine, dried and concentrated under reduced pressure to afford 0.690 g (quantitative yield) of the title compound as a brown oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted in ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-516991313e414a5f981992eb1fefee2f
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618138B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes