Sodium Azide → HCID 18617612, compound

HRID 1264201Notes

Reaction equation

HRID 1264201 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13]Cl)[CH:10]=2)[NH:5][CH:4]=1)#[N:2].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][N:15]=[N+:16]=[N-:17])[CH:10]=2)[NH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18617552HCID 18617552, compound

Product 1

HCID 18617612HCID 18617612, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.92 g (9.38 mmol) 3-cyano-5-(2-chloroethyl)indole (reference example 4) and 1.53 g (23.5 mmol) sodium azide in 10 mL DMF is heated to 80° C. for three hours, followed by azeotroping with toluene. The resulting residue is chromatographed (2:1 hexane:ethyl acetate) to provide 1.89 g of the product as a brown solid in 95% yield. 1H NMR (CDCl3): δ 3.03 (2H, t, J=7.1 Hz), 3.57 (2H, t, J=7 Hz), 7.20 (1H, dd, J=8, 1 Hz), 7.43 (1H, d, J=8 Hz), 7.62 (1H, s), 7.73 (1H, d, J=3 Hz), 8.81 (1H, br). MS (ion spray) m/z 212 (M+H)+, 169 (M−N3)+.

Workup

  1. customby azeotroping with toluene
  2. customThe resulting residue is chromatographed (2:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-24c6606d12254ffbbbdf8900ff1f45ca
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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