Pyrrolidine → 1-[5-Bromo-6-(pyrrolidine-1-sulfonyl)-2,3-dihydro-indol-1-yl]-ethanone

HRID 1475307Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:17])=[C:10]([S:13](Cl)(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>C1COCC1>[Br:17][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[S:13]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)(=[O:15])=[O:14])[N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 1-acetyl-5-bromo-2,3-dihydro-1H-indole-6-sulfonyl chloride (0.25 g, 0.74 mmol), pyrrolidine (0.156 g, 2.2 mmol) and THF (10 mL) was stirred at 20° C. for 18 h then was partitioned between water (50 mL) and EtOAc (2×50 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid. Chromatography (SiO2; gradient elution with 50-100% EtOAc in petrol) gave the title compound (0.206 g) as a colourless solid. MS: [M+H]+=373.

Workup

customthen was partitioned between water (50 mL) and EtOAc (2×50 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
customevaporated in vacuo
customto give a solid
washChromatography (SiO2; gradient elution with 50-100% EtOAc in petrol)

Sources & evidence

ORD record: ord-50bcfad73aed459fbdc18128cc9ca326
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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