HCID 67192798, compound → HCID 136019215, compound

HRID 403328Notes

Reaction equation

HRID 403328 reaction equation
[N:1]1([CH2:6][C:7]2[N:11]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[N:17]([CH3:21])[CH:16]=[CH:15]4)[C:10]([C:22]3[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[C:25]([O:31]CC4C=CC=CC=4)=[CH:24][C:23]=3[O:39]CC3C=CC=CC=3)=[N:9][N:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>CCO.[Pd]>[N:1]1([CH2:6][C:7]2[N:11]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[N:17]([CH3:21])[CH:16]=[CH:15]4)[C:10]([C:22]3[CH:27]=[C:26]([CH:28]([CH3:29])[CH3:30])[C:25]([OH:31])=[CH:24][C:23]=3[OH:39])=[N:9][N:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 67192798HCID 67192798, compound

Product 1

HCID 136019215HCID 136019215, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate (D) obtained above was subjected to Pd (10%) catalyzed hydrogenation in 10 mL EtOH for 24 hours. Removal of Pd/C and solvent gave 5-[3-imidazol-1-ylmethyl-5-(2,4-dihydroxy-5-isopropyl-phenyl)-[1,2,4]triazol-4-yl]-1-methyl-1H-indole (E) as light brown solid (0.07 g, 0.16 mmol, 80%). 1H NMR (300 MHz, DMSO-d6), δ (ppm): 11.06 (s, 1H); 9.75 (s, 1H); 7.63 (d, J=8.1 Hz, 1H); 7.57 (d, J=2.1 Hz, 1H); 7.52 (d, J=3.0 Hz, 1H); 7.28 (s, 1H); 7.03 (dd, J=8.1 Hz, 2.1 Hz, 1H); 6.94 (d, J=1.2 Hz, 1H); 6.84 (d, J=1.2 Hz, 1H); 6.51 (d, J=3.0 Hz, 1H); 6.37 (s, 1H); 6.33 (s, 1H); 5.27 (s, 2H); 3.86 (s, 3H); 2.78 (hept, J=6.6 Hz, 1H); 0.55 (d, J=6.6 Hz, 6H). ESMS calcd. for C24H25N6O2 (M+H)+: 429.3. Found: 429.3.

Workup

  1. customfor 24 hours
  2. customRemoval of Pd/C and solvent

Sources & evidence

ORD record
ord-79fc788754034d2b8c9c38993e81e6cc
Source dataset
uspto-grants-2014_06
Patent number
US08748424B2

Reaction notes

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