Tetrahydrofuran → 1-(1-(6-(1-(2-ethoxyethyl)-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

HRID 512849노트

반응식

HRID 512849 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[N:10][C:9]([N:12]3[CH2:17][CH2:16][CH:15]([N:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=5)[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH:3]=[N:2]1.[CH2:28]([O:30][CH2:31][CH2:32]Br)[CH3:29].C1COCC1.[H-].[Na+]>CCOCC.O.CN(C=O)C>[CH2:28]([O:30][CH2:31][CH2:32][N:1]1[CH:5]=[C:4]([C:6]2[N:11]=[N:10][C:9]([N:12]3[CH2:17][CH2:16][CH:15]([N:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=5)[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH:3]=[N:2]1)[CH3:29]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 896139441-(1-(6-(1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

생성물 1

HCID 763111101-(1-(6-(1-(2-ethoxyethyl)-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21584184Diethylether water용매

실험 절차

To a mixture of 1-(1-(6-(1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline (55 mg, 0.15 mmol, 1.0 equiv) and 2-ethoxyethylbromide (0.17 mL, 1.5 mmol, 10 equiv) was added THF (2 mL) and DMF (0.5 mL). NaH (30 mg, 60% in mineral oil, 0.75 mmol, 5 equiv) was then added. The resulting mixture was stirred at room temperature for 1.5 h and then poured into Et2O/H2O (20 mL/20 mL). The organic layer was washed with brine (20 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue was purified by column using 90-100% EtOAc/hexane as the eluent to yield 1-(1-(6-(1-(2-ethoxyethyl)-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline.

후처리

  1. washThe organic layer was washed with brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed
  5. customthe resulting residue was purified by column

출처 및 근거

ORD 기록
ord-0d17f6b4a32c499f882eb99c70bb1555
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102669B2

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