Sodium periodate → 3,5-Dichloro-4-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzaldehyde

HRID 626806ノート

反応式

HRID 626806 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=C)[CH:5]=[C:4]([Cl:10])[C:3]=1[N:11]1[CH:28]=[C:14]2[C:15]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23][N:22]=3)=[N:16][CH:17]=[C:18]([F:19])[C:13]2=[N:12]1.I([O-])(=O)(=O)=[O:30].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:10])[C:3]=1[N:11]1[CH:28]=[C:14]2[C:15]([NH:20][C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23][N:22]=3)=[N:16][CH:17]=[C:18]([F:19])[C:13]2=[N:12]1)[CH:8]=[O:30]

参加物

6

反応物 2

HCID 23667635Sodium periodateHCID 69671745[2-(2,6-Dichloro-4-vinylphenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)amine

生成物 1

HCID 866970833,5-Dichloro-4-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzaldehyde収率 66%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

To a mixture of [2-(2,6-dichloro-4-vinylphenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)amine (193 mg, 0.47 mmol) in acetone (10 mL) and water (2.5 mL) was added osmium (VIII) oxide (2.5% wt in tert-butanol, 0.465 mL), followed by sodium periodate (257 mg, 1.2 mmol) and the reaction mixture was stirred at room temperature overnight. The resultant mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (80% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (129 mg, 66% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.77 (s, 1H), 10.10 (s, 1H), 9.35 (d, J=2.6 Hz, 1H), 8.70 (s, 1H), 8.37 (s, 1H), 8.31 (s, 2H), 8.01 (d, J=3.5 Hz, 1H), 2.45 (s, 3H).

後処理

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (80% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-c9507adf141c41bcbbd005cf311435d8
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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