2,2-Difluoro-2-(fluorosulfonyl)acetic acid → 6-chloro-3-(2-(difluoromethoxy)ethoxy)-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588162Notes

Reaction equation

HRID 588162 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([O:31][CH2:32][CH2:33][OH:34])=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.[F:35][C:36]([F:44])(S(F)(=O)=O)C(O)=O>>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([O:31][CH2:32][CH2:33][O:34][CH:36]([F:44])[F:35])=[N:10][N:11]([C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 1182723382-((6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)oxy)ethanol

Product 1

HCID 1182722626-chloro-3-(2-(difluoromethoxy)ethoxy)-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridineYield 59%

Procedure

In a manner similar to that previously described (e.g. synthesis of Intermediate 59B/Step 2), 2-((6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)oxy)ethanol was reacted with 2,2-difluoro-2-(fluorosulfonyl)acetic acid (copper(I) iodide, acetonitrile, 80° C. 30 min) to provide 6-chloro-3-(2-(difluoromethoxy)ethoxy)-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine 59% yield) as a white crystalline solid. MS: [M+H]+ m/z 520.

Sources & evidence

ORD record
ord-4300b546f82f402083eabb74b1324153
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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