Dichloromethane → HCID 86630184, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[NH:7][N:6]=1)=[O:4].C(Cl)Cl.[H-].[Na+].Cl[C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[N:7]([C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:6]=1)=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Suspension of 5-nitro-1H-indazole-3-carboxylic acid methyl ester 18AP (7 g, 31.67 mmol) in THF (130 ml) and DCM (15 ml) was added to a NaH (60% in Mineral Oil, 1.61 g, 41.17 mmol) at 0° C. H2 gas was evolved. Chlorotriphenyl methane (8.83 g, 31.67 mmol) was added after stirring for 20 min at 0° C. Reaction mixture was subjected to heat at 60° C. for overnight. It was then cooled to room temperature and concentrated under reduced pressure. Solid was redissolved in DCM and filtered. Filtrate was concentrated under reduced pressure to give desired 5-nitro-1-trityl-1H-indazole-3-carboxylic acid methyl ester 19AP (12.95 g, 88%).
Workup
- customReaction mixture
- temperatureto heat at 60° C. for overnight
- temperatureIt was then cooled to room temperature
- concentrationconcentrated under reduced pressure
- dissolutionSolid was redissolved in DCM
- filtrationfiltered
- concentrationFiltrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8b916e4a85a047a79eb085103a7ec3ac
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546404B2
Reaction notes
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