HCID 86008498, compound → HCID 82048421, compound

HRID 1696497Notes

Reaction equation

HRID 1696497 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([C:3](=[O:4])[C:2]([F:18])([F:1])[F:17])[CH2:6][CH2:7]2

Participants

4

Reactant 1

HCID 86008498HCID 86008498, compound

Product 1

HCID 82048421HCID 82048421, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 2,2,2-trifluoro-1-(5-nitroindolin-1-yl)ethanone (7.92 g, 30.4 mmol) in MeOH (100 mL) was added 10% Pd/C (0.648 g, 0.609 mmol) and the slurry was stirred under H2 (1 atm) overnight. The mixture was filtered through a pad of Celite® and the filtrate was concentrated and dried under vacuum to give 7.7 g (crude yield>100%) of 1-(5-aminoindolin-1-yl)-2,2,2-trifluoroethanone as a yellow-brown solid. 1HNMR (400 MHz, CDCl3): δ 8.00 (d, J=8.8 Hz, 1H), 6.59 (s, 1H), 6.57 (d, J=8.4 Hz, 1H), 4.23 (t, J=8.0 Hz, 2H), 3.69 (brs, 2H), 3.16 (t, J=8.2 Hz, 2H); MS (ESI) m/z: 231.0 (M+H+).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-bca23ea88e914976801b0ed851f64d3e
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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