Ammonium formate → HCID 136055975, compound

HRID 1726084Notes

Reaction equation

HRID 1726084 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][CH2:33][CH2:32][CH2:31]1)=[CH:22][CH:21]=2)C1C=CC=CC=1.C([O-])=O.[NH4+]>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][CH2:33][CH2:34][CH2:35]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 136055985HCID 136055985, compound

Product 1

HCID 136055975HCID 136055975, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 360 mg of 5-benzyloxy-3-[5-(2-piperidin-1-ylethoxy)-1H-indol-2-yl]-1H-indazole, 916 mg of ammonium formate and 120 mg of palladium in 10 ml of ethanol is placed in a reactor that is irradiated in a microwave field (Synthwave 402) at a temperature of 90° C. for 30 minutes and the reaction mixture is then filtered through a bed of celite. The filtrate is evaporated under reduced pressure and the residue is then-taken up in a mixture of ethyl acetate (150 ml) and of water (50 ml). A 30% ammonium hydroxide solution is added so as to bring the pH to 10. After separation by settling out and extraction with ethyl acetate (1×50 ml), the organic extracts are combined, dried over magnesium sulfate and then evaporated under reduced pressure. 193 mg of 3-[5-(2-piperidin-1-ylethoxy)-1H-indol-2-yl]-1H-indazol-5-ol are isolated and characterized.

Workup

  1. customis placed in a reactor
  2. customthat is irradiated in a microwave field (Synthwave 402) at a temperature of 90° C. for 30 minutes
  3. filtrationthe reaction mixture is then filtered through a bed of celite
  4. customThe filtrate is evaporated under reduced pressure
  5. additionthe residue is then-taken up in a mixture of ethyl acetate (150 ml) and of water (50 ml)
  6. additionA 30% ammonium hydroxide solution is added so as
  7. customAfter separation
  8. extractionextraction with ethyl acetate (1×50 ml)
  9. dry with materialdried over magnesium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b623fd9c923749019dd9458d7110a6ab
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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