HCID 9973705, compound → HCID 10362645, compound

HRID 1376117Notes

Reaction equation

HRID 1376117 reaction equation
C([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[C:14]([F:24])[CH:13]=[CH:12][CH:11]=2)=[O:7])(C)(C)C.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].ClCCl>>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[F:24][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:16]([NH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[C:8]([C:6]([OH:7])=[O:5])[NH:9]2

Participants

3

Reactant 2

HCID 9973705HCID 9973705, compoundHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 10362645HCID 10362645, compoundYield 88%

Procedure

Stir at ambient temperature for 3 h a solution of 4-fluoro-3-(4-pyridinylamino)-1H-indole-2-carboxylic tert-butyl ester (Example 17, 0.15 g, 0.458 mmol) in 35% trifluoroacetic acid/dichloromethane. Concentrate the reaction under vacuum to obtain a gray solid. Dry the solid at 40° C. under vacuum and then triturate with hot ethyl acetate. Allow to cool to ambient temperature and collect a light gray powder. Dry the powder at 45° C. under vacuum for 2 h and obtain 0.15 g (88%) of the title compound: MS 272(M+H), m.p. 231–234° C. (dec.)

Workup

  1. concentrationConcentrate
  2. customthe reaction under vacuum
  3. customto obtain a gray solid
  4. customDry the solid at 40° C. under vacuum
  5. customtriturate with hot ethyl acetate
  6. customcollect a light gray powder
  7. customDry the powder at 45° C. under vacuum for 2 h

Sources & evidence

ORD record
ord-fc05a4391cc24b4fa45409c2a6a27b96
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

Loading…