Diisopropylethylamine → N-(6-fluoro-2,3-dihydro-3-benzofuranyl)-6-nitro-2-quinolinamine

HRID 1928885Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[F:15][C:16]1[CH:25]=[CH:24][C:19]2[CH:20]([NH2:23])[CH2:21][O:22][C:18]=2[CH:17]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[F:15][C:16]1[CH:25]=[CH:24][C:19]2[CH:20]([NH:23][C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=4)[N:3]=3)[CH2:21][O:22][C:18]=2[CH:17]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-chloro-6-nitro-quinoline (1.6 g, 7.67 mmol) in N-methyl-2-pyrrolidinone (15 ml) with the above described rac-6-fluoro-2,3-dihydro-benzofuran-3-ylamine (1.3 g, 8.43 mmol) and N-ethyldiisopropylamine (1.96 ml, 11.5 mmol) was stirred at 140° C. for 2 h. Cooled to room temperature, poured onto water and extracted twice with Ethyl acetate, dried over sodium sulfate and evaporated totally to give a crude product which was purified by silica gel column chromatography with heptane/dichloromethane followed by trituration with diethyl ether to give the title compound as a yellow solid (1.0 g, 40%); MS (ISP) m/e=326.2 (M+H+).

Workup

temperatureCooled to room temperature
additionpoured onto water
extractionextracted twice with Ethyl acetate
dry with materialdried over sodium sulfate
customevaporated totally
customto give a crude product which
customwas purified by silica gel column chromatography with heptane/dichloromethane

Sources & evidence

ORD record: ord-e0a4d37c27aa4c88a918ed10c026aa0c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183380B2

Reaction notes

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