Sodium Azide → 7-(2-Azido-ethoxy)-1-(3-chloro-benzyl)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazole

HRID 2240060Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:19])=[CH:12][C:13]=2[O:15][CH2:16][CH2:17]Cl)[C:8]([S:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[N:7]1.[N-:36]=[N+:37]=[N-:38].[Na+]>CS(C)=O.O>[N:36]([CH2:17][CH2:16][O:15][C:13]1[CH:12]=[C:11]([F:19])[CH:10]=[C:9]2[C:14]=1[N:6]([CH2:5][C:4]1[CH:33]=[CH:34][CH:35]=[C:2]([Cl:1])[CH:3]=1)[N:7]=[C:8]2[S:20]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:22])=[N+:37]=[N-:38]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-(3-chloro-benzyl)-7-(2-chloro-ethoxy)-5-fluoro-3-(naphthalene -1-sulfonyl)-1H-indazole (0.1 g, 0.19 mmoles) and sodium azide (0.014 g, 0.22 mmoles) in DMSO (3 mL) was stirred together in a round bottom flask under nitrogen at 90° C. for 3 hours. Reaction mixture was cooled to room temperature, diluted with water, extracted with EtOAC, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.09 g, 0.17 mmoles).

Workup

customReaction mixture
temperaturewas cooled to room temperature
extractionextracted with EtOAC
washwashed with water (2×), brine (1×)
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-f63e95884ceb4480b6ded01e3aee5098
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723329B2

Reaction notes

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