Hydrochloric Acid → 4-Fluoro-3-(6-isopropyl-quinolin-8-yl)-benzoic acid

HRID 857300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857300
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.OB(O)[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[F:22])[C:16]([OH:18])=[O:17].C([O-])([O-])=O.[Na+].[Na+].Cl.[CH2:31](O)[CH2:32][CH3:33]>[NH4+].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:21]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[C:9]1[CH:8]=[C:7]([CH:32]([CH3:33])[CH3:31])[CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 7047QuinolineHCID 10340Sodium CarbonateHCID 218655933-Borono-4-fluorobenzoic acid

Produkt 1

HCID 218655434-Fluoro-3-(6-isopropyl-quinolin-8-yl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A mixture of Quinoline 1 (1.0 eq), the 3-dihydroxylboranyl-4-fluoro-benzoic acid from Step 1 (1.2 eq), Pd(PPh3)4 (0.05 eq) and aqueous Na2CO3 (2.0M; 4.0 eq) in propanol (0.1M) was stirred at 90° C. for 12 h. The resulting mixture was cooled to room temperature, poured in saturated aqueous NH4Cl, the pH was adjusted to 5 with HCl (10%) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered. Upon concentration the desired compound crystallized and was isolated by filtration.

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationUpon concentration the desired compound
  6. customcrystallized
  7. customwas isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d250f205cf274b0fb1dbf8a9b43abdd5
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144896B2

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