Sodium Carbonate → HCID 178424919, Verbindung

HRID 251648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251648
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[CH3:20])=[C:4]([O:21][CH:22]([CH3:24])[CH3:23])[CH:3]=1.[CH:25]([C:28]1[C:36]2[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][C:31]=2[NH:30][N:29]=1)([CH3:27])[CH3:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[CH:22]([O:21][C:4]1[C:5]([CH2:9][O:10][C:11]2[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=2[CH3:20])=[C:6]([CH3:8])[N:7]=[C:2]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:36]=2[C:28]([CH:25]([CH3:27])[CH3:26])=[N:29][NH:30]3)[CH:3]=1)([CH3:24])[CH3:23]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 865939916-Chloro-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridineHCID 178440403HCID 178440403, Verbindung

Produkt 1

HCID 178424919HCID 178424919, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-chloro-4-isopropoxy-3-(5-isopropyl-2-methyl-phenoxymethyl)-2-methyl-pyridine (185 mg, 0.53 mmol), 3-isopropyl-1H-indazole-4-boronic acid (109 mg, 0.53 mmol), Pd(PPh3)4 (31 mg, 0.027 mmol), and Na2CO3 (169 mg, 1.6 mmol) in dioxane (8 mL) and water (2 mL) is heated for 24 hours at 100° C. The mixture is poured into water and extracted with EtOAc. The combined extract are dried (Na2SO4) and concentrated in vacuo. The residue is purified by flash chromatography (elution with MeOH/CH2Cl2 1:10) to yield 4-[4-isopropoxy-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyridin-2-yl]-3-isopropyl-1H-indazole. 1H NMR (CDCl3) 9.95 (br s, 1H), 7.45 (d, 1H), 7.39 (t, 1H), 7.13 (d, 1H), 7.09 (d, 1H), 6.92 (m, 2H), 6.78 (d, 1H), 5.20 (s, 2H), 4.68 (m, 1H), 3.19 (m, 1H), 2.88 (m, 1H), 2.64 (s, 3H), 2.20 (s, 3H), 1.99 (d, 6H), 1.24 (d, 6H), 1.11 (d, 6H). LCMS (m/z): 472.63 (MH)+

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe combined extract
  3. dry with materialare dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (elution with MeOH/CH2Cl2 1:10)

Quellen und Nachweise

ORD-Eintrag
ord-7d378f50dae94e65bca17964d149e7aa
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863454B2

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