Sodium Cyanide → 5,7-Dimethyl-1H-indazole-3-carbonitrile
Reaction equation
I[C:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[C:8]([CH3:11])[CH:9]=2)[NH:4][N:3]=1.[C:13]([Cu])#[N:14].[C-]#N.[Na+].OP([O-])(O)=O.[K+]>CN1C(=O)CCC1.CCOCC>[CH3:11][C:8]1[CH:9]=[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=1)[NH:4][N:3]=[C:2]2[C:13]#[N:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
Iodide 3 (20 g, 74.0 mmol) was dissolved in anhydrous NMP (300 mL). To this solution were added CuCN (19.9 g, 222 mmol, 3 eq) and NaCN (7.25 g, 148 mmol, 2 eq) and the mixture was heated at 130 ° C. for 18 h under an inert atmosphere. This solution was then poured into 0.25 M KH2PO4 (1.5 L) and Et2O (750 mL) and Celite (˜100g) were added. The suspension was stirred vigorously for 0.5 h then filtered through a sintered glass funnel. The phases were separated and the aqueous layer extracted with Et2O (3×200 mL). The combined organic extracts were washed with H2O (2×200 mL), brine (1×200 mL), dried (MgSO4), filtered and concentrated provide 8.3g (65% yield) of 5,7-dimethyl-1H-indazole-3-carbonitrile 4. The nitrile was used as is for the next reaction. RP-HPLC Method: 2-100% B in 2 minutes.
Workup
- additionwere added
- filtrationthen filtered through a sintered glass funnel
- customThe phases were separated
- extractionthe aqueous layer extracted with Et2O (3×200 mL)
- washThe combined organic extracts were washed with H2O (2×200 mL), brine (1×200 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-76abe814324241acac7324d5ca8287c1
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06984652B2
Reaction notes
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