Cesium carbonate → 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 60909

Reaktionsgleichung

Reaktionsgleichung von HRID 60909
Br[C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.CN[C@H]1CCCC[C@@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]([N:13]2[N:14]=[CH:15][CH:16]=[N:12]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 2280802-Bromo-5-methylbenzoic acidHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 178418936HCID 178418936, Verbindung

Produkt 1

HCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acidAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-bromo-5-methylbenzoic acid (2.0 g, 9.30 mmol), 1,2,3-triazole (1.08 mL, 18.6 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (2.23 mL, 13.95 mmol), Cs2CO3 (4.55 g, 13.95 mmol) and CuI (124 mg, 0.65 mmol) in DMF (12 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The reaction was cooled to rt, diluted with MeOH, and acidified with AcOH to pH 4-5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a yellow oil (1.5 g, 61%). MS (ESI) 204 (M+H).

Aufarbeitung

  1. customwas degassed
  2. temperatureThe reaction was cooled to rt
  3. additiondiluted with MeOH
  4. customThe solvent was removed in vacuo
  5. customto obtain the crude which
  6. customwas purified by silica gel chromatography (0˜100% DCM/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-f9bf1d451c994de585039736b601cfed
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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