5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → 1-(Oxan-2-yl)-1H-indazol-5-amine

HRID 1771404Notes

Reaction equation

HRID 1771404 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[CH:7]2)([O-])=O>CCOC(C)=O.[Pd]>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[N:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

4

Reactant 1

HCID 151476265-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 229339271-(Oxan-2-yl)-1H-indazol-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.00 g, 4.04 mmol) in EtOAc (10 mL) was degassed for 10 min and then placed under vacuum and filled with nitrogen. The reaction mixture was placed under vacuum again, palladium on carbon (10% wt./wt, 272 mg, 0.256 mmol) was added and the resulting mixture was stirred under an atmosphere of hydrogen at RT for 20 hr. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to yield the title compound, Intermediate D1 as a pale yellow solid (553 mg, 2.47 mmol, 61% yield); Rt 1.38 min, Basic method, m/z 218.3 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) δ: 1.52-1.58 (2H, over-lapping m), 1.71 (1H, m), 1.90 (1H, m), 2.01 (1H, m), 2.36 (1H, m), 3.68 (1H, m), 3.86 (1H, m), 4.85 (2H, s), 5.67 (1H, dd), 6.74 (1H, m), 6.81 (1H, dd), 7.40 (1H, m), 7.75 (1H, d).

Workup

  1. additionfilled with nitrogen
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-809122bb0bc74d69b1b54c8e61415c99
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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