(E)-N-(4-(difluoromethoxy)phenyl)-6-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)pyridazin-3-amine → N-(4-(difluoromethoxy)phenyl)-6-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)pyridazin-3-amine

HRID 77493Notes

Reaction equation

HRID 77493 reaction equation
[F:1][CH:2]([F:34])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:12]=[N:13][C:14](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:23]=[CH:22]4)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1>C(OCC)(=O)C.[Pd]>[F:34][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:12]=[N:13][C:14]([CH2:17][CH2:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:23]=[CH:22]4)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 86679786(E)-N-(4-(difluoromethoxy)phenyl)-6-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)pyridazin-3-amine

Product 1

HCID 86679787N-(4-(difluoromethoxy)phenyl)-6-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)pyridazin-3-amineYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-N-(4-(difluoromethoxy)phenyl)-6-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)pyridazin-3-amine (0.14 g, 0.302 mmol) in ethyl acetate (5 mL) was added Pd—C (0.064 g, 0.604 mmol and the reaction mixture was stirred at room temperature under H2 for 3 h. The reaction mixture was filtered through pad of celite, washed with ethyl acetate, and the filtrate was concentrated to give N-(4-(difluoromethoxy)phenyl)-6-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)pyridazin-3-amine as a yellow solid (0.13 g, 80%). LCMS (ES-API), m/z 466.6 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through pad of celite
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fa8a752a6dfa4ae880f336a7d4d20644
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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