Sodium Azide → 3-(3-azidopropyl)-5-chloro-1H-indole

HRID 1777525Notes

Reaction equation

HRID 1777525 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][CH:6]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][CH:6]=1)=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 668318443-(3-bromopropyl)-5-chloro-1H-indole

Product 1

HCID 866993903-(3-azidopropyl)-5-chloro-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3-bromopropyl)-5-chloro-1H-indole (0.730 g; 2.68 mmol) and sodium azide (0.522 g; 8.03 mmol) was stirred in DMF (5 mL) for 18 hours and was then concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. After separation, the organic layer was dried over magnesium sulfate and the volatiles were evaporated under reduced pressure to give quantitatively 3-(3-azidopropyl)-5-chloro-1H-indole as an oily residue which was used without purification in the next step.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. customThe residue was partitioned between water and dichloromethane
  3. customAfter separation
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customthe volatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-607e49c0ad95427d91256582a9ef2e60
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…