Hydrochloric Acid → 5-Bromo-6-(pyrrolidine-1-sulfonyl)-2,3-dihydro-1H-indole

HRID 1475308Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:13])=[O:12])[N:7](C(=O)C)[CH2:6][CH2:5]2.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:12])=[O:13])[NH:7][CH2:6][CH2:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[5-bromo-6-(pyrrolidine-1-sulfonyl)-2,3-dihydro-indol-1-yl]-ethanone (0.203 g, 0.54 mmol), concentrated hydrochloric acid (2 mL) and 1,4-dioxane (5 mL) was heated at 100° C. in a sealed vessel for 2 h. The mixture was cooled then neutralised with saturated aqueous sodium hydrogen carbonate and resulting solid collected by filtration to give the title compound (0.13 g, 72%). MS: [M+H]+=331.

Workup

temperatureThe mixture was cooled
customresulting solid
filtrationcollected by filtration

Sources & evidence

ORD record: ord-fd0f2cb9c0f14cec95ecd74254b8ba8d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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