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

HRID 1507115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507115
[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-626d0a5e448b4072a6b2badc6e3b0aea
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221793B2

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