Lithium Hexamethyldisilazide → HCID 86620628, compound
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:28][C:29]1[N:36]=[C:35](F)[C:34]([F:38])=[CH:33][C:30]=1[C:31]#[N:32]>C1COCC1>[C:31]([C:30]1[CH:33]=[C:34]([F:38])[C:35]([NH:1][C:2]2[N:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[N:5]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:3]=2)=[N:36][C:29]=1[F:28])#[N:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of tert-butyl 5-amino-3-isopropoxy-1H-pyrazole-1-carboxylate (Method 78, 4.0 g, 16.4 mmol) in THF (45 ml) was cooled to −78° C. A 1.0M THF solution of LiHMDS (2.61 g, 15.6 mmol) was added dropwise and the reaction was stirred at −78° C. for 30 minutes. A −78° C. solution of 2,5,6-trifluoronicotinonitrile (1.3 g, 8.2 mmol) in THF (20 ml) was added dropwise via cannula to the above anion solution. Upon completion of the addition, the resulting reaction was allowed to stir for 10 minutes at −78° C., and was then quenched with water (100 ml). The reaction was allowed to warm to room temperature, extracted with DCM (3×100 ml), dried (Na2SO4), filtered, and then concentrated to give the title compound (95% conversion by LCMS) which was used without further purification. MS: Calcd.: 379. Found: [M+H]+ 380.
Workup
- additionUpon completion of the addition
- customthe resulting reaction
- stirringto stir for 10 minutes at −78° C.
- customwas then quenched with water (100 ml)
- temperatureto warm to room temperature
- extractionextracted with DCM (3×100 ml)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-41ee5ccccd084af2a3cc7a3cd03b5bd2
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835465B2
Reaction notes
Loading…