4,5,6,7-Tetrafluoro-1H-indole-3-carbaldehyde → HCID 178513724, compound

HRID 527277Notes

Reaction equation

HRID 527277 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]([NH2:17])=[O:16].[F:18][C:19]1[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]2[C:20]=1[C:21]([CH:31]=O)=[CH:22][NH:23]2.[BH4-].[Na+]>CCO.N1CCCCC1>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]([NH2:17])=[O:16])=[C:2]([NH:1][CH2:31][C:21]3[C:20]4[C:24](=[C:25]([F:30])[C:26]([F:29])=[C:27]([F:28])[C:19]=4[F:18])[NH:23][CH:22]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 27767024,5,6,7-Tetrafluoro-1H-indole-3-carbaldehydeHCID 4311764Sodium borohydrideHCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513724HCID 178513724, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide (100 mg) was then suspended in EtOH (4 mL) and 4,5,6,7-tetrafluoro-1H-indole-3-carbaldehyde (1 eq.) and piperidine (1 drop) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain product as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr. Resulting imine was suspended in 5 mL MeOH and sodium borohydride (3 eq.) was added. HPLC confirmed reaction was complete (absence of imine). After completion (1 hr), precipitate was filtered to obtain D22 as a light yellow powder as product. Product was washed with deionized water to remove excess sodium borohydride.

Workup

  1. temperatureat reflux until intermediate
  2. customAfter reaction
  3. custom(18 hrs) it
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto obtain product as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr
  9. customreaction
  10. filtrationAfter completion (1 hr), precipitate was filtered
  11. customto obtain D22 as a light yellow powder as product
  12. washProduct was washed with deionized water
  13. customto remove excess sodium borohydride

Sources & evidence

ORD record
ord-d652ca67d388432f8c3de5d568093a7a
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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