o-Fluoro-beta-nitrostyrene → 3-(1-(2-Fluorophenyl)-2-nitroethyl)-6-methyl-5-(pyrimidin-5-yloxy)-1H-indole

HRID 2361251Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:11][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1/[CH:25]=[CH:26]/[N+:27]([O-:29])=[O:28]>C(Cl)Cl>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([CH3:1])=[C:3]([O:11][C:12]3[CH:13]=[N:14][CH:15]=[N:16][CH:17]=3)[CH:4]=2)[NH:8][CH:7]=1)[CH2:26][N+:27]([O-:29])=[O:28]

Participants

Conditions

Temperature: 130 °C

Procedure

6-Methyl-5-(pyrimidin-5-yloxy)-1H-indole (0.1783 g, 0.792 mmol) and (E)-1-fluoro-2-(2-nitrovinyl)benzene (0.159 g, 0.950 mmol) were dissolved in CH2Cl2, and the solution was concentrated in vacuo. The residue was heated at 130° C. for 4 hr, and the crude product was purified by flash chromatography using an ISCO 40 g column eluting with 0-5% MeOH/CH2Cl2. Appropriate fractions were collected and concentrated in vacuo to give the desired product (0.1644 g, 0.419 mmol, 52.9% yield) as a tan foam.

Workup

concentrationthe solution was concentrated in vacuo
customthe crude product was purified by flash chromatography
washeluting with 0-5% MeOH/CH2Cl2
customAppropriate fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-028f3e8fb5ab48feb11ee1b943482ecb
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

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