Water → HCID 86588916, compound

HRID 1008655Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:47])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[N:15]([CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:36][CH2:37]OS(C)(=O)=O)=[CH:6][C:5]=1[O:43][CH:44]([CH3:46])[CH3:45].[N-:48]=[N+:49]=[N-:50].[Na+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:47])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[N:15]([CH:23]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:14]=2[CH2:36][CH2:37][N:48]=[N+:49]=[N-:50])=[CH:6][C:5]=1[O:43][CH:44]([CH3:46])[CH3:45]

Participants

Conditions

Temperature: 60 °C

Procedure

The mesylate from Step 5 (0.115 g, 0.17 mmol) was dissolved in DMF (5 mL). NaN3 (0.065 g, 1.0 mmol) was added and the mixture was heated to 60° C. and stirred for three hours. Reaction was cooled to room temperature and water was added. Extracted with EtOAc and washed organic layer with brine. Dried organics over sodium sulfate and filtered and concentrated by rotary evaporation. Dried further under a strong vacuum. Obtained 0.100 g of 4-{2-[2-(2-Azido-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-2-isopropoxy-benzoic acid methyl ester in 94% yield.

Workup

customReaction
temperaturewas cooled to room temperature
extractionExtracted with EtOAc
washwashed organic layer with brine
filtrationDried organics over sodium sulfate and filtered
concentrationconcentrated by rotary evaporation
customDried further under a strong vacuum

Sources & evidence

ORD record: ord-cdd82d56e2d84bb78e8033627cff7e9f
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797708B2

Reaction notes

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