Potassium Hydroxide → HCID 58081154, compound

HRID 2364950Notes

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 poured into ice water. The resulting aqueous mixture was extracted with diethylether (3×), dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The crude residue thus obtained was purified by column chromatography (silica gel; 0-10% DCM/heptane 1:1 as eluent). The desired fractions were collected and evaporated in vacuo to yield D17 (2.897 g, 19.93%) as a white solid.

Workup

customprepared
extractionThe resulting aqueous mixture was extracted with diethylether (3×)
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent was evaporated in vacuo
customThe crude residue thus obtained
customwas purified by column chromatography (silica gel; 0-10% DCM/heptane 1:1 as eluent)
customThe desired fractions were collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-8ab734755a284a7aa5e22b054eba38ba
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697689B2

Reaction notes

Loading…