Triethylamine → 3-[5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-1H-indazol-5-ol

HRID 1726100Notes

Reaction equation

HRID 1726100 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([O:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[CH:22][CH:21]=2)C1C=CC=CC=1.C([O-])=O.[NH4+].C(N(CC)CC)C>C(O)C.[Pd]>[N:30]1([CH2:29][CH2:28][O:27][C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([C:12]2[C:11]4[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=4)[NH:14][N:13]=2)=[CH:26]3)[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723923Ammonium formateHCID 136055970HCID 136055970, compound

Product 1

HCID 1360560083-[5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-1H-indazol-5-olYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
67 °C

Procedure

1.12 g of 5-benzyloxy-3-[5-(2-morpholin-4-ylethoxy)-1H-indol-2-yI]-1H-indazole are dissolved in 55 ml of absolute ethanol and then 424 mg of palladium-on-charcoal, 587 mg of ammonium formate and 227 μl of triethylamine are successively added. The reaction medium is stirred at 67° C. (internal temperature of the suspension). A substantial amount of gas is seen to be given off. After stirring for one hour, the medium is filtered through paper and the catalyst is rinsed with absolute ethanol. The filtrate is concentrated under vacuum to obtain 558 mg of 3-[5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-1H-indazol-5-ol.

Workup

  1. stirringAfter stirring for one hour
  2. filtrationthe medium is filtered through paper
  3. washthe catalyst is rinsed with absolute ethanol
  4. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-21225314d1ea48419cfaa57a6d2bfa49
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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