Iodine → HCID 178452208、化合物

HRID 387580ノート

反応式

HRID 387580 の反応式
[I:1]I.[C:3]1([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[C:11]3[CH:17]=[N:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+].[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOCC>[I:1][C:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]=2[N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]2)[NH:15][N:16]=1

参加物

7

反応物 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 68758199tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 178452208HCID 178452208、化合物収率 95.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

I2 (0.421 g, 1.66 mmol) was added to a solution of tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.63 g, 0.830 mmol) and KOH (0.140 g, 2.49 mmol) (crushed by mortar and pestle) in DMF (10 mL). The resulting mixture was heated to 60° C. for 3 hours. Ether (20 mL) and saturated Na2SO3 (10 mL) were added. The organic layer was separated, washed with brine, and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.40 g, 95%) as a solid. MS APCI (+) m/z 506.2 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.30 (s, 1H), 7.60 (m, 3H), 7.49 (m, 2H), 3.63 (m, 4H), 2.95 (m, 4H), 1.51 (s, 9H).

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-2f801f359cd2482d82bfb0a37cbecd8f
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

反応ノート

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