Ammonium formate → 5-[2-(tetrahydro-pyran-4-ylmethyl)-piperazin-1-yl]-1H-indazole

HRID 1672156Notes

Reaction equation

HRID 1672156 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[CH:17]3)[CH:10]([CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[O:27]1[CH2:28][CH2:29][CH:24]([CH2:23][CH:10]2[CH2:9][NH:8][CH2:13][CH2:12][N:11]2[C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[CH:17]3)[CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57825833HCID 57825833, compound

Product 1

HCID 497982435-[2-(tetrahydro-pyran-4-ylmethyl)-piperazin-1-yl]-1H-indazoleYield 62%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 5-[4-benzyl-2-(tetrahydro-pyran-4-ylmethyl)-piperazin-1-yl]-1H-indazole (0.27 g, 0.7 mmol), Pd(OH)2 (0.050 g), in 75 mL MeOH was added ammonium formate (0.43 g, 6.9 mmol). The mixture was heated to reflux. After 1 hr the mixture was cooled, filtered through celite and concentrated in vacuo to give a crude solid. Purification via flash chromatography afforded 5-[2-(tetrahydro-pyran-4-ylmethyl)-piperazin-1-yl]-1H-indazole (0.13 g, 62%) as a white foam: 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=0.9 Hz, 1H), 7.40 (dd, J=9.6, 0.9 Hz, 1H), 7.23-7.11 (m, 2H), 3.94-3.80 (m, 2H), 3.63-3.52 (m, 2H), 3.37-2.89 (m, 8H), 1.68-0.97 (m, 7H)

Workup

  1. temperatureThe mixture was heated to reflux
  2. temperatureAfter 1 hr the mixture was cooled
  3. filtrationfiltered through celite and
  4. concentrationconcentrated in vacuo
  5. customto give a crude solid
  6. customPurification via flash chromatography

Sources & evidence

ORD record
ord-5e32ebc07eb0489c8598075a23b56b39
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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