6-vinyl-1H-indazole → 6-ethyl-1H-indazole

HRID 246036

Reaction equation

HRID 246036 reaction equation
[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[CH:5][CH:4]=1)=[CH2:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 866779366-vinyl-1H-indazole

Product 1

HCID 189494906-ethyl-1H-indazoleYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-vinyl-1H-indazole (350 mg, 2.42 mmol) in MeOH (24 ml) was added 10% Pd on carbon (wet, 443 mg). The reaction mixture was stirred under an atmosphere of hydrogen (balloon) for 2.5 h then filtered over Celite, rinsing with EtOAc. The filtrate was concentrated to afford 305 mg (86%) of 6-ethyl-1H-indazole as a white semi-solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.04 (s, 1H), 7.67 (d, J=8.3 Hz, 1H), 7.32 (s, 1H), 7.06 (d, J=8.3 Hz, 1H), 2.80 (q, J=7.6 Hz, 2H), 1.31 (t, J=7.6 Hz, 3H).

Workup

  1. filtrationthen filtered over Celite
  2. washrinsing with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b9a877b43b0349cbab63a6bb3407eb36
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

Loading…