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

HRID 512849ノート

反応式

HRID 512849 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21584184Diethylether water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0d17f6b4a32c499f882eb99c70bb1555
出典データセット
uspto-grants-2015_08
特許番号
US09102669B2

反応ノート

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