Ammonium formate → 1-(1-(2,2-Dimethoxyethyl)-1H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

HRID 2387501ノート

反応式

HRID 2387501 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27])[N:19]=[CH:18]3)[C:11](=[O:30])[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:29][O:28][CH:25]([O:26][CH3:27])[CH2:24][N:20]1[C:21]2[C:17](=[CH:16][C:15]([N:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]3=[O:30])=[CH:23][CH:22]=2)[CH:18]=[N:19]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 592933874-(Benzyloxy)-1-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yl)pyridin-2(1H)-one

生成物 1

HCID 592934031-(1-(2,2-Dimethoxyethyl)-1H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one収率 95%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

A solution of 4-(benzyloxy)-1-(1-(2,2-Dimethoxyethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (4.96 g, 12.2 mmol) and ammonium formate (1.53 g, 24.4 mmol) in CH3OH was stirred for 10 min. Pd/C (5.5 g) was added under a nitrogen atmosphere. The reaction mixture was heated at 80° C. for 2 h and then allowed to cool. The mixture was filtered through a layer of Celite, and the filtrate was concentrated. The residue was triturated with MeOH, concentrated to dryness, triturated with EtOAc, sonicated for 20 min and then concentrated to give the title compound (3.62 g, 95%) as a yellow/white solid: 1H NMR (500 MHz, CDCl3) 8.06 (s, 1H), 7.68 (s, 1H), 7.58 (d, J=8.9 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.27 (d, 1H, overlapping with solvent peak), 6.12 (s, 1H), 6.05 (d, J=7.3 Hz, 1H), 4.78 (t, J=5.2 Hz, 2H), 4.50 (d, J=5.2 Hz, 2H), 3.38 (s, 6H).

後処理

  1. temperatureto cool
  2. filtrationThe mixture was filtered through a layer of Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was triturated with MeOH
  5. concentrationconcentrated to dryness
  6. customtriturated with EtOAc
  7. customsonicated for 20 min
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-d091da6c73a84ea683f89578de9dfe15
出典データセット
uspto-grants-2012_09
特許番号
US08268868B2

反応ノート

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