Reaction equation
[F:1][C:2]1[C:10]([CH:11]=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[NH2:13]/[C:14](/[CH3:18])=[CH:15]\[C:16]#[N:17]>C(O)(=O)C.C(OCC)(=O)C>[F:1][C:2]1[C:10]([CH:11]2[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:2]([CH3:10])=[C:3]2[C:4]#[N:5])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
250 mg (1.52 mmols) 4-fluoro-1H-indazole-5-carbaldehyde (Synthetic Preparation 11) and 250.1 mg (3.05 mmols) 3-aminocrotononitrile were dissolved in 1.74 mL acetic acid and refluxed for 1.5 hours. The mixture was allowed to cool to room temperature, filtered and washed with a little amount of acetic acid. The product was dried under vacuum at 40° C. to yield a first crop. The mother liquors were diluted with ethyl acetate, washed with water and saturated sodium hydrogen carbonate solution and dried over sodium sulfate to yield a second crop. Together 232 mg (51, 9%) 4-(4-fluoro-1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile were obtained (Cpd. No. 311). 1H-NMR (DMSO-d6): δ=13.42 (br s, 1H), 9.58 (br s, 1H), 8.21 (s, 1H), 7.44 (d, 1H), 7.32 (dd, 1H), 4.86 (s, 1H), 2.04 (s, 6H) ppm.
Workup
- temperaturerefluxed for 1.5 hours
- filtrationfiltered
- washwashed with a little amount of acetic acid
- customThe product was dried under vacuum at 40° C.
- customto yield a first crop
- washwashed with water and saturated sodium hydrogen carbonate solution
- dry with materialdried over sodium sulfate
- customto yield a second crop
Sources & evidence
- ORD record
- ord-f2a101d93b7f48c88e932c62319b02fd
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198456B2
Linked notes
Loading…