methyl 5-formyl-1H-indazole-3-carboxylate → 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl ester

HRID 218479

Reaktionsgleichung

Reaktionsgleichung von HRID 218479
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[NH:7][N:6]=1)=[O:4].N/[C:17](=[CH:20]\[CH3:21])/[C:18]#[N:19]>CC(O)=O.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]3[C:13]([C:5]#[N:6])=[C:8]([CH3:9])[NH:7][C:20]([CH3:21])=[C:17]3[C:18]#[N:19])[CH:12]=2)[NH:7][N:6]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 24958745methyl 5-formyl-1H-indazole-3-carboxylateHCID 86589747Aminocrotononitrile

Produkt 1

HCID 249594685-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl esterAusbeute 177,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-formyl-1H-indazole-3-carboxylic acid methyl ester (92 mg, 0.45 mmol) and aminocrotononitrile (74 mg, 0.9 mmol) in HOAc (1 mL) was kept at 110° C. for 15 mins. After cooling to rt, the reaction mixture was diluted with EtOAc, washed with brine, dried, and concentrated. The crude product was purified by TLC to afford 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl ester (133 mg, 89%) (Cpd. No. 85, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=8.04 (s, 1H), 7.72 (s, 1H), 7.49 (d, 1H), 4.58 (s, 1H), 4.02 (s, 3H), 2.0 (s, 6H) ppm.

Aufarbeitung

  1. washwashed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified by TLC

Quellen und Nachweise

ORD-Eintrag
ord-4a69144bfcc8477da8286e7ef8c507b0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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