Dimethylformamide → HCID 89666801, compound

HRID 2171226Notes

Reaction equation

Cl[C:2]([F:7])([F:6])C([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[OH:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=2)[N:23]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:22]=1>C(OCC)(=O)C>[F:7][CH:2]([F:6])[O:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=2)[N:23]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium chlorodifluoroacetate (4.75 g) and potassium carbonate (8.58 g) were added to a DMF (3 ml) solution containing ethyl 3-hydroxy-5-nitro-1H-indazol-1-carboxylate (1.56 g), followed by stirring at 80° C. for 1 hour. The reaction solution was adjusted to room temperature and ethyl acetate was added to remove an insoluble precipitate. The organic layers were washed with a saturated ammonium chloride aqueous solution, water, and saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1). A yellow solid of ethyl 3-(difluoromethoxy)-5-nitro-1H-indazol-1-carboxylate (1.14 g) was thus obtained.

Workup

customwas adjusted to room temperature
customto remove an insoluble precipitate
washThe organic layers were washed with a saturated ammonium chloride aqueous solution, water, and saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationThen, the solvent was distilled away under reduced pressure
customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record: ord-774e3fb620fa411f93233090eaedd795
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051310B2

Reaction notes

Loading…