HCID 59293415, compound → HCID 59293407, compound

HRID 2387503Notes

Reaction equation

HRID 2387503 reaction equation
[CH3:1][O:2][CH:3]([O:29][CH3:30])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:15]3=[O:28])=[CH:11][CH:12]=2)[CH:7]=[N:6]1>CO.[Pd]>[CH3:30][O:29][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:16][C:15]3=[O:28])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

4

Reactant 1

HCID 59293415HCID 59293415, compound

Product 1

HCID 59293407HCID 59293407, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-1-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yl)-4-styrylpyridin-2(1H)-one (2.08 g, 5.19 mmol) was stirred in CH3OH (100 mL) for 2 h under nitrogen atmosphere. Palladium on carbon (3.1 g) was added under nitrogen atmosphere, and the mixture was stirred for 20 min. The nitrogen line was then replaced with a H2 balloon and the reaction mixture was stirred under an H2 atmosphere at room temperature for 2 h and then flushed with nitrogen (10 min). The mixture was filtered through a layer of Celite, and the filtrate was concentrated. The residue was triturated with MeOH and concentrated to gave the title compound (1.77 g, 84%) as a orange solid 1H NMR (300 MHz, CDCl3) 8.04 (s, 1H), 7.68 (d, J=15 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.44-7.36 (dd, J=8.9, 1.9 Hz, 1H), 7.36-7.28 (m, 2H, overlapping with solvent peak), 7.26-7.18 (m, 3H), 6.51 (s, 1H), 6.16-6.06 (dd, J=7.0, 1.8 Hz, 1H), 4.76 (t, J=5.3 Hz, 2H), 4.48 (t, J=5.3 Hz, 2H), 3.36 (s, 6H) 3.01-2.90 (m, 2H), 2.90-2.76 (m, 2H).

Workup

  1. stirringthe reaction mixture was stirred under an H2 atmosphere at room temperature for 2 h
  2. customflushed with nitrogen (10 min)
  3. filtrationThe mixture was filtered through a layer of Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was triturated with MeOH
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-532b9f743c7e4f1695da7d12e9640d07
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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