p-Toluenesulfonic acid → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid

HRID 2367697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367697
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([OH:13])=[O:12].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[N:6]=[C:5]2[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acid2×HCID 80803,4-dihydro-2H-pyran2×HCID 71573585-bromo-1H-indazole-3-carboxylic Acid

Produkt 1

HCID 698056555-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acidAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-bromo-1H-indazole-3-carboxylic acid (CXV) (59.8 g, 248 mmol) in THF (800 mL) under argon was added 3,4 dihydro-2H-pyran (50.6 mL, 558 mmol) and p-TsOH (4.72 g, 24.8 mmol). The reaction was heated to reflux at 60° C. for 16 h. An additional portion of p-TsOH (0.025 eq) and 3,4 dihydro-2H-pyran (0.56 eq) was added and the reflux continued for 5 h. The solution was concentrated under vacuum. EtOAc was added to the residue and the suspension was filtered and dried under high vacuum overnight to produce 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid (CXVIII) as a white solid (49.07 g, 150.9 mmol, 60.8% yield). ESIMS found for C13H13BrN2O3 m/z 326.3 (M+H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. concentrationThe solution was concentrated under vacuum
  3. additionEtOAc was added to the residue
  4. filtrationthe suspension was filtered
  5. customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-4dd9615f77334af897f54dd3fd46a5da
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697887B2

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