Water → 1-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indole

HRID 1890364Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[F:13][CH:14]([F:26])[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>CN(C)C=O>[F:26][CH:14]([F:13])[O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:24])=[O:23])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Iodo-1H-indole (2.0 g, 8.23 mmol) was dissolved in dimethylformamide (DMF) (10 ml) and cooled to 0° C. Sodium hydride (494 mg, 12.34 mmol) was added in small portions. The reaction mixture was stirred for 1 hour at 0° C. 4-(Difluoro-methoxy)-benzenesulfonyl chloride (2.196 g, 9.05 mmol) was dissolved in DMF (5 ml), and added slowly to the reaction mixture. Stirring was continued for 45 minutes. Cold water (150 ml) was added to the reaction mixture. The reaction mixture was extracted twice with ethyl acetate (100 ml). The organic layer was dried over magnesium sulphate, filtered, and the solvent evaporated under reduced pressure to give a crystalline solid (3.0 g, 81%). ESI-MS [m/z]: 449.95 [M+H]+. 1H-NMR (500 MHz, d6-DMSO): δ=8.05 (d, 2H), 8.0 (s, 1H), 7.85 (d, 1H), 7.8 (d, 1H), 7.65 (d, 1H), 7.4 (t, J=70 Hz, 1H), 7.35 (d, 2H), 6.8 ppm (d, 1H).

Workup

additionadded slowly to the reaction mixture
stirringStirring
waitwas continued for 45 minutes
extractionThe reaction mixture was extracted twice with ethyl acetate (100 ml)
dry with materialThe organic layer was dried over magnesium sulphate
filtrationfiltered
customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record: ord-f769e013773543daa41273c834202e0a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507469B2

Reaction notes

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