Potassium Carbonate → 2-(4-((4-(6-Amino-1H-indazol-1-yl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 515379ノート

反応式

HRID 515379 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=3)[CH:9]=[N:8]2)[CH2:3][CH2:2]1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[N:8][N:7]2[CH:4]2[CH2:3][CH2:2][N:1]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:34])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])=[CH:23][CH:24]=3)[CH2:6][CH2:5]2)=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 671937121-(Piperidin-4-yl)-1H-indazol-6-amine

生成物 1

HCID 866710002-(4-((4-(6-Amino-1H-indazol-1-yl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol収率 42.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-(Piperidin-4-yl)-1H-indazol-6-amine (3.33 mmol, 0.721 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (3.33 mmol, 1.124 g) and potassium carbonate (6.67 mmol, 0.921 g) were combined and stirred overnight at room temperature in acetonitrile (15 mL). The reaction mixture was concentrated at reduced pressure and the resulting residue taken up in dichloromethane. The organic phase was washed with water and dried over sodium sulfate. The solvent was removed and the resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 8% methanol/dichloromethane) to afford the title compound (664 mg). MS (ESI) m/z 473.5 [M+H]+

後処理

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. customthe resulting residue was purified by silica chromatography (
  6. washeluting with a solvent gradient from dichloromethane to 8% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-e5d893517d504c4fa2433c588797a809
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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