Iodine → HCID 178451733、化合物

HRID 68748

反応式

HRID 68748 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:23]I.[OH-].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([I:23])=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 674494164-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 178451733HCID 178451733、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (9.70 g, 3.24 mmol) in DMF (32 mL) at room temperature was treated with iodine (1.23 g, 4.86 mmol) and KOH (grounded, 454 mg, 8.1 mmol). The resulting mixture was stirred at room temperature for 40 min, then treated with saturated Na2S2O3 aqueous solution. The resulting mixture was then extracted with EtOAc (3×). The combined extracts were washed with brine and dried over Na2SO4. The resulting mixture was filtered and concentration under reduced pressure. The resulting residue was purified by flash chromatography on silica-gel (gradient eluant 10% to 40% EtOAc in heptane) to yield the title compound as white solid.

後処理

  1. extractionThe resulting mixture was then extracted with EtOAc (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe resulting mixture was filtered
  5. concentrationconcentration under reduced pressure
  6. customThe resulting residue was purified by flash chromatography on silica-gel (gradient eluant 10% to 40% EtOAc in heptane)

出典と根拠

ORDレコード
ord-98c16b4a4f534f93ada601a2380dd571
出典データセット
uspto-grants-2014_09
特許番号
US08822447B2

関連ノート

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