Ammonium formate → (1-Ethyl-3-methyl-1H-indazol-5-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine

HRID 1094396Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([N+]([O-])=O)=[CH:22][CH:23]=2)[C:18]([CH3:28])=[N:17]1)[CH3:15].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([NH:11][CH2:10][CH2:9][C:6]3[CH:7]=[N:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=3)=[CH:22][CH:23]=2)[C:18]([CH3:28])=[N:17]1)[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (6-trifluoromethyl-pyridin-3-yl)-acetonitrile (849 mg, 4.14 mmol, prepared as per example 47, step 1) and 1-ethyl-3-methyl-5-nitro-1H-indazole (700 mg, 3.76 mmol) in MeOH (10 mL) was treated with ammonium formate (5 eq.) and 10% Pd/C (140 mg) and stirred at 80° C. for 2 h. Filtration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (794 mg, 61%) as a light yellow oil. MS m/e: 349.1 [M+H]+.

Workup

filtrationFiltration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record: ord-43bfc9b5d33a4a568f633cdf9e6ccf9d
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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