Cesium carbonate → 4-Benzyl-9-methyl-7-(2-methyl-5-nitro-phenyl)-4,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one

HRID 2261192Notes

Reaction equation

[CH2:1]([N:8]1[CH:13]=[C:12]([CH:14]=O)[C:11]([NH:16][CH3:17])=[C:10]2[CH:18]=[CH:19][N:20]=[C:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:23](=[O:35])[CH2:24][C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[CH3:34].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([N:8]1[CH:13]=[C:12]2[C:11]([N:16]([CH3:17])[C:23](=[O:35])[C:24]([C:25]3[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=3[CH3:34])=[CH:14]2)=[C:10]2[CH:18]=[CH:19][N:20]=[C:9]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 7-benzyl-4-methylamino-7H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (400 mg, 1.5 mmol), (2-methyl-5-nitro-phenyl)-acetic acid methyl ester (350 mg, 1.67 mmol) and cesium carbonate (1.1 g, 3 mmol) in 5 ml anhydrous DMF is heated to 120° C. for 30 min. The reaction mixture is cooled down to room temperature. The reaction mixture is partitioned in water and ethyl acetate, extracted with ethyl acetate three times. The organic phase is combined and washed with brine, dried over Na2SO4. The crude product is purified by silica gel flash chromatography, eluted with 40% to 100% ethyl acetate in hexane to give the title compound as light yellow solid. MS m/z 426.2 (M+1).

Workup

temperatureThe reaction mixture is cooled down to room temperature
customThe reaction mixture is partitioned in water
extractionethyl acetate, extracted with ethyl acetate three times
washwashed with brine
dry with materialdried over Na2SO4
customThe crude product is purified by silica gel flash chromatography
washeluted with 40% to 100% ethyl acetate in hexane

Sources & evidence

ORD record: ord-1acf6e3ab03b4e65b132fd7e8dae851c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846923B2

Reaction notes

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