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

HRID 925316Notes

Reaction equation

HRID 925316 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]

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-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole was prepared according to method D Step IV with 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); the yield was quantitative as a brown oil.

Sources & evidence

ORD record
ord-4f5e77ec10e847bcb6f8bb6384c0ffd1
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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