Heptane → 1,4-dichloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyridazine

HRID 42225

反応式

HRID 42225 の反応式
Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[C:7]([Cl:11])[N:6]=[N:5][C:4]=1[Cl:12].[C:13](=[O:16])([O-])[O-].[Na+].[Na+].C[C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.CCCCCCC>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:12][C:4]1[C:3]2[CH2:2][N:25]([CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:16][CH3:13])=[CH:21][CH:22]=3)[CH2:9][C:8]=2[C:7]([Cl:11])=[N:6][N:5]=1

参加物

7

反応物 4

HCID 8900HeptaneHCID 10340Sodium CarbonateHCID 660354-MethylbenzylamineHCID 574716294,5-Bis(bromomethyl)-3,6-dichloropyridazine

生成物 1

HCID 592405361,4-dichloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyridazine収率 41%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

To a suspension of 4,5-bis(bromomethyl)-3,6-dichloropyridazine (800 mg, 2.39 mmol) in 40 mL anhydrous THF was added with sodium carbonate (507 mg, 4.78 mmol) and tetrabutylammonium iodide (88.3 mg, 0.24 mmol). The reaction mixture was added with 4-methylbenzylamine (0.31 mL, 2.39 mmol) in 20 mL THF dropwisely for 2 h. The reaction mixture was heated at 70° C. for 8 h and concentrated. The crude material was dissolved in DCM and washed with water and brine. The organic solution was dried over Na2SO4 and concentrated to afford a crude oil. The mixture was purified by flash chromatography on silica gel, eluting with 10-80% EtOAc:heptane to afford a off-white solid (300 mg, yield: 41%).

後処理

  1. concentrationconcentrated
  2. dissolutionThe crude material was dissolved in DCM
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated
  6. customto afford a crude oil
  7. customThe mixture was purified by flash chromatography on silica gel
  8. washeluting with 10-80% EtOAc

出典と根拠

ORDレコード
ord-5a00fc92a557426b89643e8e79018b9c
出典データセット
uspto-grants-2013_09
特許番号
US08536168B2

関連ノート

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