HCID 59128664, compound → HCID 59128695, compound

HRID 1991128Notes

Reaction equation

HRID 1991128 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([CH:16]=[C:17]([CH3:19])[CH3:18])[CH:14]=3)[N:9]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:8]=2)[CH:4]=[N:3]1>CO.[OH-].[OH-].[Pd+2]>[CH2:16]([C:13]1[CH:14]=[C:15]2[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:8][N:9]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:10]2=[N:11][CH:12]=1)[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 59128664HCID 59128664, compound

Product 1

HCID 59128695HCID 59128695, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of olefin 61 (118 mg, 3.00 mmol) and moist Pd(OH)2 on carbon (96 mg of catalyst containing 20% wt Pd) in MeOH (6 mL) was stirred vigorously under H2 for 93 h. The catalyst was removed by filtration through a pad of Celite. The pad was washed sequentially with MeOH, CH2Cl2 and AcOH and the combined filtrates were concentrated to afford azaindole 62 as brown oil that was used directly without purification in the next step. 1H NMR (400 MHz; CDCl3) δ 0.90 (s, 3H), 0.91 (s, 3H), 1.87 (m, 1H), 2.58 (d, J=7.2 Hz, 2H), 3.96 (s, 3H), 7.34 (s, 1H), 7.41-7.46 (m, 2H), 7.50-7.55 (m, 1H), 7.59 (s, 1H), 7.62-7.67 (m, 2H), 7.73 (s, 1H), 7.86 (d, J=1.8 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H).

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. washThe pad was washed sequentially with MeOH, CH2Cl2 and AcOH
  3. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-9f3c9bed563f42559f705d6c9d9a9da8
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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