Water → HCID 86588916, compound

HRID 2237147Notes

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-dab686c4957b46848a41f6af32d680a4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713964B2

Reaction notes

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