Trifluoroacetic acid → HCID 67093668, compound

HRID 1630880Notes

Reaction equation

HRID 1630880 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](=[O:32])(=[O:31])[N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH:23]=1)=O)(C)(C)C.FC(F)(F)C(O)=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](=[O:31])(=[O:32])[N:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[CH:21]=[N:20][CH:19]=3)[NH:8]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67093740HCID 67093740, compound

Product 1

HCID 67093668HCID 67093668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-2-(5-diethylsulfamoyloxy-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester is redissolved in DCM (2 mL) and trifluoroacetic acid (2 mL) is added. After 1 h, saturated aqueous sodium bicarbonate is added and following extraction with dichloromethane, the organic layer is dried over sodium sulfate and concentrated to give diethyl-sulfamic acid 5-(6-chloro-1H-indol-2-yl)-pyridin-3-yl ester, which is used in the next step without further purification. MS (ESI) m/z 378.1 (M+H)+

Workup

  1. extractionextraction with dichloromethane
  2. dry with materialthe organic layer is dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b391959dc8b54ddf84b0bacb1d59a804
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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