Dimethylformamide → 6-Nitro-1-pyrimidin-5-ylmethyl-1H-indole
Reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:13]1[C:21]2[C:16](=[CH:17]C=CC=2)[CH:15]=[CH:14]1.[H-].[Na+].S([O-])(=O)(=O)C.C[N:30](C=O)C>>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:15][C:16]2[CH:21]=[N:13][CH:14]=[N:30][CH:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Conditions
- Temperature
- -40 °C
Procedure
6-Nitroindole-1H-indole (35.6 g, 220 mmol) was dissolved in 750 mL of DMF and NaH (50%, 12 g, 250 mmol) was added in portions and the mixture was stirred for 1 hour. The mixture was cooled to −40° C. and the solution of the mesylate was added dropwise. The mixture was allowed to reach room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate (2×). The combined organic layers were washed with water (2×) and brine and dried over Na2SO4. After concentration in vacuo the material was purified by means of column chromatography (silica, heptane/ethyl acetate (1:1)→(1:4)) affording compound the title compound as a yellow solid (14 g, 55 mmol, 39%).
Workup
- waitto reach room temperature overnight
- customThe mixture was quenched with water
- extractionextracted with ethyl acetate (2×)
- washThe combined organic layers were washed with water (2×) and brine
- dry with materialdried over Na2SO4
- concentrationAfter concentration in vacuo the material
- customwas purified by means of column chromatography (silica, heptane/ethyl acetate (1:1)→(1:4))
Sources & evidence
- ORD record
- ord-e73bbad352994074b066227ec2d7c5da
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124647B2
Reaction notes
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