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Water → Methyl 4-amino-3-chloro-6-(1,3-benzoxazol-6-yl)pyridine-2-carboxylate

HRID 708933
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 708933
[NH2:1][C:2]1[CH:7]=[C:6](Br)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13].CC1(C)C(C)(C)OB([C:22]2[CH:30]=[CH:29][C:25]3[N:26]=[CH:27][O:28][C:24]=3[CH:23]=2)O1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([C:22]2[CH:30]=[CH:29][C:25]3[N:26]=[CH:27][O:28][C:24]=3[CH:23]=2)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 22677536Methyl 4-amino-6-bromo-3-chloropicolinateHCID 712398486-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo(d)oxazole

Produkt 1

HCID 71240046Methyl 4-amino-3-chloro-6-(1,3-benzoxazol-6-yl)pyridine-2-carboxylateAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

0.024 g (0.03 mmol) of (PPh3)2PdCl2 is added to a solution of 0.3 g (1.13 mmol) of methyl 4-amino-6-bromo-3-chloropyridine-2-carboxylate in 20 ml of dioxane, and this mixture is stirred at RT for 30 min. In succession, 0.28 g (1.13 mmol) of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazole, 0.47 g (3.4 mmol) of K2CO3 and 2 g (111 mmol) of H2O are then added to this mixture, which is then stirred under reflux for 6 h. The mixture is allowed to stand at RT for a further 12 h and then added to 40 ml of H2O. This mixture is extracted repeatedly with CH2Cl2, and the combined organic phase is dried over Na2SO4 and then concentrated. Purification by chromatography on silica gel using the mobile phase heptane/ethyl acetate (3/7) gives 0.1 g (29%) of product. 1H-NMR (CDCl3): δ 8.25 (s, 1H, benzoxazole), 8.15 (s, 1H, benzoxazole), 7.90, 7.80 (2d, 2H, benzoxazole), 7.20 (s, 1H, pyridine), 4.80 (bs, 2H, NH2), 4.00 (s, 3H, COOCH3).

Aufarbeitung

  1. stirringis then stirred
  2. temperatureunder reflux for 6 h
  3. waitto stand at RT for a further 12 h
  4. extractionThis mixture is extracted repeatedly with CH2Cl2
  5. dry with materialthe combined organic phase is dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by chromatography on silica gel using the mobile phase heptane/ethyl acetate (3/7)

Quellen und Nachweise

ORD-Eintrag
ord-e64c0ce7fe3843a1bc6989d71b3a24d7
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09179676B2

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