Trifluoroacetic acid → pyrrolidine-1-sulfonic acid 5-(6-chloro-1H-indol-2-yl)-pyridin-3-yl ester

HRID 593616Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[C:9]1[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][S:25]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)(=[O:27])=[O:26])[CH:23]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[C:9]([C:18]3[CH:23]=[C:22]([O:24][S:25]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)(=[O:27])=[O:26])[CH:21]=[N:20][CH:19]=3)[NH:8]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-Chloro-2-[5-(pyrrolidine-1-sulfonyloxy)-pyridin-3-yl]-indole-1-carboxylic acid tert-butyl ester is dissolved in DCM (2 mL), and the mixture is cooled to 0° C. TFA (2 mL) is added and the mixture is stirred at room temperature for 1 h. Saturated sodium bicarbonate is then added and the mixture is extracted with DCM. The organic layer is dried over sodium sulfate and concentrated in vacuo to afford pyrrolidine-1-sulfonic acid 5-(6-chloro-1H-indol-2-yl)-pyridin-3-yl ester as an oil which is taken onto the next step without further purification. MS (ESI) m/z 376.2 (M+H)+.

Workup

extractionthe mixture is extracted with DCM
dry with materialThe organic layer is dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4d0baf2990584d7b86feafd3d1f1174a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242963B2

Reaction notes

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