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

HRID 706659

Reaktionsgleichung

Reaktionsgleichung von HRID 706659
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=O)C>[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 dried 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 (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 DMF (30 mL) and tetramethylstannane (0.04 mL, 0.28 mmol) were added, followed by triethylamine (0.04 mL, 0.30 mmol). The flask was 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 dried flask equipped with a reflux condenser
  2. additionwere added
  3. customThe flask was 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-72093760061844b8a8bf218d3475ab3c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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