Ammonium formate → 3-[5-(2-diethylaminoethoxy)-1H-indol-2-yl]-1H-indazol-5-ol

HRID 1726091Notes

Reaction equation

HRID 1726091 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]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:22][CH:21]=2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[CH2:33]([N:30]([CH2:31][CH3:32])[CH2:29][CH2:28][O:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:12]1[C:11]3[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=3)[NH:14][N:13]=1)=[CH:26]2)[CH3:34]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 136056003{2-[2-(5-benzyloxy-1H-indazol-3-yl)-1H-indol-5-yloxy]ethyl}diethylamine

Product 1

HCID 1360559783-[5-(2-diethylaminoethoxy)-1H-indol-2-yl]-1H-indazol-5-olYield 44.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 320 mg of {2-[2-(5-benzyloxy-1H-indazol-3-yl)-1H-indol-5-yloxy]ethyl}diethylamine, 32 mg of palladium-on-charcoal at 10%, and 180 mg of ammonium formate is irradiated in a Synthwave 402 microwave oven at atmospheric pressure for 35 minutes at 75° C. at 5% power, and then for 10 minutes at 20% power. The catalyst is filtered through a bed of celite, and the filtrate is evaporated under reduced pressure. The compound obtained is taken up in ethyl acetate (20 ml) and a saturated sodium bicarbonate solution (20 ml), separated by settling out, dried over magnesium sulfate and then evaporated under reduced pressure to obtain 115 mg of 3-[5-(2-diethylaminoethoxy)-1H-indol-2-yl]-1H-indazol-5-ol, which is characterized.

Workup

  1. customis irradiated in a Synthwave 402 microwave oven at atmospheric pressure for 35 minutes at 75° C. at 5% power
  2. filtrationThe catalyst is filtered through a bed of celite
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe compound obtained
  5. customa saturated sodium bicarbonate solution (20 ml), separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-02a367ee6e184d578234ddde01560190
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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