1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanone → 2-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)propan-2-ol

HRID 588137Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.[CH3:35][Mg]Br>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])([CH3:35])[CH3:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In an oven dried flask and under a nitrogen gas atomosphere, 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanone (39B, 110 mg, 0.235 mmol) was dissolved in THF (2.0 ml) cooled to −78° C. and charged with methylmagnesium bromide (0.470 ml, 0.470 mmol). The reaction was allowed to stir for 1 hr, eventually reaching 0° C. The reaction was slowly quenched with saturated ammonium chloride (3 mL) and partioned between EtOAc 2×10 mL, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide 2-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)propan-2-o (Intermediate 40B). The products were carried forward without purification. MS: [M+H]+ m/z 484.

Workup

customIn an oven dried flask
customeventually reaching 0° C
customThe reaction was slowly quenched with saturated ammonium chloride (3 mL)
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0d9b1cc5c7304ee58315bfe31cc5e182
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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