HCID 10587390, compound → HCID 10823326, compound

HRID 1696498Notes

Reaction equation

HRID 1696498 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][N:5]2[C:3](=[O:4])[C:2]([F:18])([F:1])[F:17])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 10587390HCID 10587390, compound

Product 1

HCID 10823326HCID 10823326, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 2,2,2-trifluoro-1-(6-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 yield 1-(6-aminoindolin-1-yl)-2,2,2-trifluoroethanone (7.7 g, crude yield>100%) as a yellow-brown solid. 1H-NMR (400 MHz, CDCl3): δ 7.64 (d, J=2.0 Hz, 1H), 7.01 (d, J=8.0 Hz, 1H), 6.49 (dd, J=8.4, and 2.0 Hz, 1H), 4.24 (t, J=8.0 Hz, 2H), 3.85 (brs, 2H), 3.13 (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-1a04649abec1438b95097de391b0f759
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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