HCID 59128699, compound → HCID 59128686, compound

HRID 1991130Notes

Reaction equation

HRID 1991130 reaction equation
[Si]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[CH:14]=[C:15]2[C:21]([C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)=[CH:20][N:19]([S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:16]2=[N:17][CH:18]=1)(C(C)(C)C)(C)C>CO.[OH-].[OH-].[Pd+2]>[CH3:27][N:25]1[CH:26]=[C:22]([C:21]2[C:15]3[C:16](=[N:17][CH:18]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:14]=3)[N:19]([S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:29])=[O:30])[CH:20]=2)[CH:23]=[N:24]1

Participants

4

Reactant 1

HCID 59128699HCID 59128699, compound

Product 1

HCID 59128686HCID 59128686, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of olefin 65 (198 mg, 0.38 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 43 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 66 as brown oil that was used directly without purification in the next step; 1H NMR (400 MHz; CDCl3) δ 1.55-1.76 (m, 4H), 2.71 (t, J=7.7 Hz, 2H), 3.64 (t, J=6.4 Hz, 2H), 3.97 (s, 3H), 7.43-7.47 (m, 2H), 7.52-7.56 (m, 1H), 7.64 (s, 1H), 7.71 (s, 1H), 7.73-7.75 (m, 2H), 8.16-8.18 (m, 2H), 8.27 (d, J=1.9 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-07c7e94398d04c2b81c4a5f36903e7cd
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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