Potassium Carbonate → 6-chloro-3-(difluoro-methoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588180Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:30])[NH:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.Cl[C:32]([F:38])([F:37])C(OC)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([O:30][CH:32]([F:38])[F:37])=[N:9][N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3 (2H)-one (Intermediate 3B; 368 mg, 0.893 mmol) and methyl 2-chloro-2,2-difluoroacetate (0.5 mL, 4.74 mmol) in DMF (2 mL) was charged with K2CO3 (2.5 g, 18.09 mmol) at room temperature. The reaction was stirred at 80° C. for 30 min. The reaction mixture was diluted with H2O and filtered to give 6-chloro-3-(difluoro-methoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine, which was carried onto the next step without further purification. MS ESI calc'd. For C26H18ClF2N3O [M+1]+ 462. found 462.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-410cb54207bd4422986120b8c5cf5554
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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