Sodium Carbonate → 3-Methyl-5-pyridin-3-yl-3H-benzooxazol-2-one

HRID 1253915

Reaktionsgleichung

Reaktionsgleichung von HRID 1253915
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17](=[O:19])[N:16]([CH3:20])[C:15]=2[CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:20][N:16]1[C:15]2[CH:21]=[C:11]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:12]=[CH:13][C:14]=2[O:18][C:17]1=[O:19]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 3374695-bromo-3-methyl-3H-benzooxazol-2-oneHCID 27343783-Pyridinylboronic acid

Produkt 1

HCID 498017123-Methyl-5-pyridin-3-yl-3H-benzooxazol-2-oneAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of pyridin-3-ylboronic acid (61.5 mg, 0.5 mmol), 5-Bromo-3-methyl-3H-benzooxazol-2-one (114 mg, 0.5 mmol), polymer-supported Pd(PPh3)4 (0.11 mmol/g, 114 mg, 0.0125 mmol), Na2CO3 (2 M in water, 0.5 mL, 1 mmol) in DME (3 mL) was heated to reflux for 6 hrs. After filtration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 1-3%) and yielded the title compound as pale yellow solid (45 mg). 1HNMR(CDCl3, 400.342 MHz): δ 3.47 (s, 3H), 7.13 (s, 1H), 7.30 (m, 2H), 7.38 (dd, J=4.8, 7.9 Hz, 1H), 7.85 (m, 1H), 8.62 (dd, J=1.5, 4.8 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 6 hrs
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 1-3%)

Quellen und Nachweise

ORD-Eintrag
ord-68922bd57f3b45b09a3a8933893f47ac
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455522B2

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