Hydrochloric Acid → 5-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid

HRID 2068648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068648
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].O>[F:10][C:11]1[N:12]=[CH:13][C:14]([C:2]2[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=2)=[CH:15][CH:16]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 120399785-Bromothiophene-3-carboxylic acid

Produkt 1

HCID 581101925-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-bromo-thiophene-3-carboxylic acid (0.71 g, 4.4 mmol), 2-fluoropyridine-5-boronic acid (0.619 g, 4.4 mmol), caesium carbonate (2.9 g, 8.8 mmol), and palladium tetrakis(triphenylphosphine) (0.470 g, 0.44 mmol) in DME (40 mL), IMS 20 mL) and water (10 mL) was divided across three microwave vials and each was heated by microwave irradiation to 120° C. for 20 minutes. The batches were combined and concentrated and the residue was partitioned between saturated aqueous sodium carbonate and DCM. The aqueous phase was isolated and acidified using dilute HCl (pH 2) giving a precipitate which was collected by filtration to afford the title compound as a white solid (0.815 g). LCMS m/z 224.07 [M+H]+ R.T.=2.83 min (Analytical Method 8).

Aufarbeitung

  1. concentrationconcentrated
  2. customthe residue was partitioned between saturated aqueous sodium carbonate and DCM
  3. customThe aqueous phase was isolated
  4. customgiving a precipitate which
  5. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-504463a5127247e2aa09e75cc7a60991
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299063B2

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