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

HRID 2387501노트

반응식

HRID 2387501 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d091da6c73a84ea683f89578de9dfe15
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268868B2

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