Potassium Hydroxide → HCID 58081154, compound

HRID 2361750Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[O:11]1[C:15]2([CH2:20][CH2:19][CH:18](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1.[OH-].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:18]1[CH2:19][CH2:20][C:15]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:16][CH2:17]1)[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromoindole (8.472 g, 43.216 mmol), toluene-4-sulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester (13.5 g, 43.216 mmol) (prepared according to the procedure described in Journal of the Chemical Society, Perkin Transactions 1 (2002), (20), 2251-2255) and powdered potassium hydroxide (13.239 g, 235.958 mmol) in DMSO (300 ml) was stirred at 80° C. for 6 h. Subsequently, the mixture was cooled to room temperature and poured into ice water. The resulting aqueous mixture was extracted with Et2O, dried (Na2SO4), and the volatiles were evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; DCM/heptane 1:1 as eluent). The desired fractions were collected and evaporated in vacuo to yield D29 (2.897 g, 19.93%) as a white solid.

Workup

customprepared
temperatureSubsequently, the mixture was cooled to room temperature
extractionThe resulting aqueous mixture was extracted with Et2O
dry with materialdried (Na2SO4)
customthe volatiles were evaporated in vacuo
customThe crude residue was purified by column chromatography (silica gel; DCM/heptane 1:1 as eluent)
customThe desired fractions were collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-9a161f5904934910887c3abfe1db3967
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691813B2

Reaction notes

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