Water → Tert-butyl 2-(3-cyano-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

HRID 1052112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052112
I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:3]=1.O.[CH3:21][N:22](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:21]([C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:3]=1)#[N:22]

Komponenten

6

Edukt 3

HCID 962WaterHCID 6228DimethylformamideHCID 68283706Tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

Produkt 1

HCID 68283337Tert-butyl 2-(3-cyano-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

A mixture of tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate (1.00 g, 2.55 mmol), Zn(CN)2 (329 mg, 2.55 mmol), Pd(dppf)C2 (208 mg, 0.25 mmol), Pd2(dba)3 (233 mg, 0.25 mmol), water (2.7 mL) and DMF (20 mL) was subjected to microwave irradiation at 120° C. for 30 min under argon. The reaction mixture was filtered through a pad of Celite and the filtrate was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under vacuum. The residual oil was purified by flash chromatography on silica gel (EtOAc/c-hexane 1:2 then 1:1) to give the title compound. MS (LC/MS): 273.0 [M+H]+; tR (HPLC conditions d): 3.04 min.

Aufarbeitung

  1. customirradiation at 120° C. for 30 min under argon
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. additionthe filtrate was diluted with water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. customdried (Phase separator)
  8. concentrationconcentrated under vacuum
  9. customThe residual oil was purified by flash chromatography on silica gel (EtOAc/c-hexane 1:2

Quellen und Nachweise

ORD-Eintrag
ord-f3ea9d3ffeab4a76917169886534ba40
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388199B2

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