Water → 2-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

HRID 1982789Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[C:17]1([S:14]([N:9]2[C:10]3[C:6](=[C:5]([O:4][CH2:3][CH2:2][N:23]=[N+:24]=[N-:25])[CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-(2-chloroethoxy)-1-(phenylsulfonyl)-1H-indole (3.35 g, 10 mmol) and sodium azide (1.95 g, 30 mmol) in anhydrous dimethylformamide is stirred under nitrogen for 20 hr at 60° C., poured into water and extracted with diethyl ether. The extracts are combined, washed sequentially with 1N HCl, H2O and saturated NaCl, dried over MgSO4 and concentrated in vacuo to afford the title product as an off-white solid, 3.3 g (96%), identified by NMR and mass spectral analyses.

Workup

extractionextracted with diethyl ether
washwashed sequentially with 1N HCl, H2O and saturated NaCl
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7ea0f066c6c249dfaf0dfbd177a60da6
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541358B2

Reaction notes

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