Triethylamine → 3-methyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

HRID 79250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79250
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:3]=1.[C:22]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C[Sn](C)(C)C.C(N(CC)CC)C>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].CN(C)C=O>[CH3:22][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11661TetramethyltinHCID 80271Tri-o-tolylphosphineHCID 672597623-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

Produkt 1

HCID 672592993-methyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazoleAusbeute 394,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A dry, 100 mL round bottom flask equipped with a reflux condenser and a nitrogen line was charged with 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (Example 142, Step B; 100 mg, 0.254 mmol), tri-o-tolylphosphine (15.4 mg, 0.051 mmol), and tris(dibenzylideneacetone)dipalladium (0) (23 mg, 0.025 mmol). The flask was purged with nitrogen and anhydrous N,N-dimethylformamide (30 mL), and tetramethylstannane (0.04 mL, 0.28 mmol) were added, followed by triethylamine (0.04 mL, 0.30 mmol). The flask was thoroughly degassed under nitrogen and heated at 80° C. for 6 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted multiple times with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to preparative thin-layer chromatography on silica with 2% MeOH-DCM as eluent to afford 56.8 mg of desired product as a yellow solid.

Aufarbeitung

  1. customA dry, 100 mL round bottom flask equipped with a reflux condenser
  2. additionwere added
  3. customThe flask was thoroughly degassed under nitrogen
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. additiondiluted with water
  6. extractionextracted multiple times with DCM and EtOAc
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-58f84488c8b348979457d82c21d3471b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

Notizen zur Reaktion

Wird geladen…