Potassium Carbonate → N-((1-ethyl-1H-indazol-3-yl)methyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline

HRID 2178427Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a 10 mL round-bottomed flask were added 2-((4-fluoro-3-nitrophenoxy)methyl)quinoline (50 mg, 0.17 mmol) and acetonitrile (0.84 mL). To the resulting mixture were added 1-(1-ethyl-1H-indazol-3-yl)methanamine HCl salt (37.4 mg, 0.17 mmol) and K2CO3 (81 mg, 0.59 mmol). The resulting mixture was heated to 80° C. for 3 days. The mixture was cooled to RT and concentrated to dryness. The residue was purified by FCC to give the title compound. MS (ESI): mass calcd. for C26H23N5O3, 453.18; m/z found, 454.2 [M+H]+.

Workup

temperatureThe mixture was cooled to RT
concentrationconcentrated to dryness
customThe residue was purified by FCC

Sources & evidence

ORD record: ord-158017da4bdc4f5db5f7eae3a75749f6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067917B2

Reaction notes

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