Water → 2-(1-Benzyl-1H-indol-5-yl)-N-methylethane-1-sulfonamide

HRID 1028417Notes

Reaction equation

[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([C:22]#[CH:23])[CH:9]=1)(=[O:5])=[O:4].CC(C)([O-])C.[K+].O.CCCCCCC>CN1CCCC1=O>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:11](=[CH:12][CH:13]=1)[N:14]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:23]=[CH:22]2)(=[O:4])=[O:5]

Participants

Conditions

Temperature: 82.5 °C

Procedure

2-(4-benzylamino-3-ethynyl-phenyl)-ethanesulfonic acid methylamide (100 g) was dissolved in N-methylpyrrolidone (1500 ml) at 25° C. Potassium tert-butoxide (67 g) was added and the reaction mass was heated to 80-85° C. for 120-150 minutes. The reaction mass was cooled gradually to 25° C., water (3500 ml) was added and stirred for 30 minutes. The solution was extracted with ethyl acetate (4000 ml). The organic layer was dried over sodium sulfate and distilled under vacuum to obtain a residue. The residue was treated with heptane (500 ml) to obtain a solid which was filtered, washed with heptane and dried at 50-55° C. under vacuum to obtain the title compound. (Yield: 76 g, HPLC Purity: 98%)

Workup

temperatureThe reaction mass was cooled gradually to 25° C.
extractionThe solution was extracted with ethyl acetate (4000 ml)
dry with materialThe organic layer was dried over sodium sulfate
distillationdistilled under vacuum
customto obtain a residue
customto obtain a solid which
filtrationwas filtered
washwashed with heptane
customdried at 50-55° C. under vacuum

Sources & evidence

ORD record: ord-3c1b0d5f2c4f414a955fd1164d27e3b6
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735589B2

Reaction notes

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