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

HRID 2387501Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

temperatureto cool
filtrationThe mixture was filtered through a layer of Celite
concentrationthe filtrate was concentrated
customThe residue was triturated with MeOH
concentrationconcentrated to dryness
customtriturated with EtOAc
customsonicated for 20 min
concentrationconcentrated

Sources & evidence

ORD record: ord-d091da6c73a84ea683f89578de9dfe15
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268868B2

Reaction notes

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