Ethylamine → ethyl-[4-(5-nitro-1-trityl-1H-indazol-3-yl)-pyridin-2-yl]-amine

HRID 1038103Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH2:39]([NH2:41])[CH3:40]>C1COCC1>[CH2:39]([NH:41][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1)[CH3:40]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole (800 mg, 1.6 mmol) and 2M ethyl amine in THF (20 mL) was heated in a sealed tube at 80° C. for four days. Cooled to room temperature and concentrated. The crude product was purified by column chromatography on silica get eluting with a solution of ethyl acetate in hexane (1:1) to give the title compound (300 mg, 36%).

Workup

temperatureCooled to room temperature
concentrationconcentrated
customThe crude product was purified by column chromatography on silica
customget
washeluting with a solution of ethyl acetate in hexane (1:1)

Sources & evidence

ORD record: ord-4b87ae52ca2f490c8091f8ec7c3c0460
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546404B2

Reaction notes

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