Selenium Dioxide → 3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

HRID 588107Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:13]2[C:14]([CH3:19])=[N:15][C:16]([Cl:18])=[CH:17][C:12]=2[N:11]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Se](=O)=[O:40]>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:13]2[C:14]([CH:19]=[O:40])=[N:15][C:16]([Cl:18])=[CH:17][C:12]=2[N:11]([C:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(benzyloxy)-6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine (18.72 g, 36.3 mmol) and selenium dioxide (14.42 g, 130 mmol) in dioxane (200 ml) was heated to 100° C. with attached reflux condenser for 16 hr. Added more selenium dioxide (3.35 g, 30.2 mmol) and continued to heat to 100° C. for 4.5 hr. Cooled to RT, filtered through celite, eluted with EtOAc, concentrated filtated in vacuo, took up residue in DCM, filtered through celite, eluted with DCM, concentrated filtrate in vacuo and purified via flash chromatography (0-100% EtOAc/Hex) to provide 3-(benzyloxy)-6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde. MS: [M+H]+ m/z 530.

Workup

temperatureto heat to 100° C. for 4.5 hr
temperatureCooled to RT
filtrationfiltered through celite
washeluted with EtOAc
concentrationconcentrated
filtrationfiltered through celite
washeluted with DCM, concentrated filtrate in vacuo
custompurified via flash chromatography (0-100% EtOAc/Hex)

Sources & evidence

ORD record: ord-14890083958545fc8a6562705f409fd9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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