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 2261192ノート

反応式

HRID 2261192 の反応式
[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

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 46738291Methyl 2-(2-methyl-5-nitrophenyl)acetateHCID 178482272HCID 178482272、化合物

生成物 1

HCID 591985084-Benzyl-9-methyl-7-(2-methyl-5-nitro-phenyl)-4,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1acf6e3ab03b4e65b132fd7e8dae851c
出典データセット
uspto-grants-2010_12
特許番号
US07846923B2

反応ノート

読み込み中…