Cyclohexanol → methyl 1-cyclohexyl-1H-indazole-3-carboxylate
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.[CH:14]1(O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:14]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1Participants
6
Procedure
To a mixture of methyl 1H-indazole-3-carboxylate (5.00 g), cyclohexanol (9.00 mL), triphenylphosphine (14.9 g) and tetrahydrofuran (100 mL) was added 40% diethyl azodicarboxylate toluene solution (25.6 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, diethyl ether was added to the residue, and the mixture was stirred at 0° C. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title object compound (6.84 g, 93%) as a pale-red oil.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure, diethyl ether
- additionwas added to the residue
- stirringthe mixture was stirred at 0° C
- filtrationThe precipitate was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio)
Sources & evidence
- ORD record
- ord-86826ed234a046229b5877ca30ddfe44
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436043B2
Reaction notes
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