2-(3-Hydroxymethyl-pyrazolo[1,5-a]pyridin-2-yl)-propan-2-ol → 2-(1-Hydroxy-1-methyl-1-ethyl)-pyrazolo[1,5-A]pyridine-3-carbaldehyde

HRID 549392Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:4]([C:12]([OH:15])([CH3:14])[CH3:13])=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12>O1CCCC1.[O-2].[Mn+4].[O-2]>[OH:15][C:12]([C:4]1[C:3]([CH:2]=[O:1])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 2-(3-hydroxymethyl-pyrazolo[1,5-a]pyridin-2-yl)-propan-2-ol (1.8 g, 7.42 mmol) in tetrahydrofuran (60 mL) under nitrogen atmosphere was added manganese (IV) oxide (5.22 g, 60 mmol) and the mixture was heated to 65° C. for 40 h. The mixture was filtered through a Celite pad, which was washed with excess dichloromethane. The filtrates were combined and concentrated in vacuo and the residue was purified via silica gel column chromatography (0-40% ethyl acetate in heptane) to give the title compound (1.01 g, 4.95 mmol, 67% yield) as a light yellow solid.

Workup

filtrationThe mixture was filtered through a Celite pad, which
washwas washed with excess dichloromethane
concentrationconcentrated in vacuo
customthe residue was purified via silica gel column chromatography (0-40% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-3466ebd22a8d4fea8b394e27bfa6159c
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943652B2

Reaction notes

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