2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole

HRID 512837ノート

反応式

HRID 512837 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.CCOC(C)=O>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 715715696-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

生成物 1

HCID 715852956-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline (75 mg, 0.2 mmol) in THF (3 mL) was added DDQ (54 mg, 0.24 mmol). The resulting mixture was stirred at room temperature for 30 min and was poured into EtOAc (30 mL). The organic layer washed with Na2CO3(aq) (30 mL), H2O (30 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue purified by column using 80-90-100% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to yield 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole, which was then converted to its corresponding HCl salt.

後処理

  1. washThe organic layer washed with Na2CO3(aq) (30 mL), H2O (30 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed
  5. customthe resulting residue purified by column

出典と根拠

ORDレコード
ord-66a671102de949ac93c5c54a2924daed
出典データセット
uspto-grants-2015_08
特許番号
US09102669B2

反応ノート

読み込み中…