Potassium Carbonate → Ethyl 6-[4-(cyano-dimethyl-methyl)phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboylate

HRID 971143Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:18])[NH:15][CH2:16][CH2:17][C:12]=3[C:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:10]2)=[CH:5][CH:4]=1.I[C:25]1[CH:30]=[CH:29][C:28]([C:31]([CH3:35])([CH3:34])[C:32]#[N:33])=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CS(C)=O>[C:32]([C:31]([CH3:35])([CH3:34])[C:28]1[CH:29]=[CH:30][C:25]([N:15]2[CH2:16][CH2:17][C:12]3[C:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:10][N:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[C:13]=3[C:14]2=[O:18])=[CH:26][CH:27]=1)#[N:33]

Participants

Conditions

Temperature: 130 °C

Procedure

Part D. To a DMSO (4 mL, degassed) solution of ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate (0.6 g, 1.9 mmol), and 2-(4-iodophenyl) 2-methylproprionitrile (0.6 g, 2.2 mmol), and K2CO3 (0.66 g, 4.8 mmol) and was added CuI (73 mg, 0.3 mmol). The reaction was heated to 130° C. for 18 h. The reaction was cooled, extracted with EtOAc, washed with H2O, and dried (MgSO4). Purification by chromatography on silica gel (1:1 hexanes/ethyl acetate) afforded the title compound 0.4 g (45.9%) of a pale yellow solid; Mass Spec (M+H)+ 459.3.

Workup

temperatureThe reaction was cooled
extractionextracted with EtOAc
washwashed with H2O
dry with materialdried (MgSO4)
customPurification by chromatography on silica gel (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-311282f9f3ab408bb9a0b5f3bc6cb9cd
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312214B2

Reaction notes

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