Sodium Azide → 3-(2-azidoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

HRID 58637Notes

Reaction equation

HRID 58637 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[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][CH:9]=[C:10]([C:13]#[N:14])[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]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 668319283-(2-bromoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

Product 1

HCID 866638383-(2-azidoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(2-bromoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile (0.906 g; 2.49 mmol) and sodium azide (0.486 g; 7.48 mmol) in DMF (7 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 yield 0.900 g (quantitative) 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-a68384b18541404eb8b7892d7947e035
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

Loading…