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

HRID 42225

반응식

HRID 42225 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5a00fc92a557426b89643e8e79018b9c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

연결된 노트

불러오는 중…