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Water → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-7-methyl-1H-[1,8]naphthyridin-4-one

HRID 226991
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 226991
C([Mg]Cl)(C)C.I[C:7]1[CH:8]=[C:9]([CH3:14])[C:10]([CH3:13])=[N:11][CH:12]=1.CON(C)[C:18]([C:20]1[C:29](=[O:30])[C:28]2[C:23](=[N:24][C:25]([CH3:31])=[CH:26][CH:27]=2)[N:22]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Br:39])[N:34]=2)[CH:21]=1)=[O:19].O>O1CCCC1>[Br:39][C:35]1[N:34]=[C:33]([CH2:32][N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[C:25]([CH3:31])[N:24]=3)[C:29](=[O:30])[C:20]([C:18]([C:7]3[CH:12]=[N:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH:8]=3)=[O:19])=[CH:21]2)[CH:38]=[CH:37][CH:36]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 206625845-Iodo-2,3-dimethylpyridineHCID 577545251-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 577546731-(6-Bromo-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-7-methyl-1H-[1,8]naphthyridin-4-one
Ausbeute 39,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

0.23 mL (0.469 mmol, 2M in THF) isopropylmagnesium chloride was added to a solution of 104.4 mg (0.448 mmol) of 5-iodo-2,3-dimethyl-pyridine in 1 mL of tetrahydrofuran. After the reaction was stirred for 40 min at room temperature 85 mg (0.204 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide in 0.6 mL of tetrahydrofuran was added and the reaction stirred for 1 h. Water was added and was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and dried in vacuo. The crude product was purified by flash column chromatography using 20-100% ethyl acetate in hexane to yield 37.4 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-7-methyl-1H-[1,8]naphthyridin-4-one. LC-MSD, m/z for C23H19BrN4O2 [M+H]: 463.07 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 1.7 min

Aufarbeitung

  1. additionwas added
  2. extractionwas extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customdried in vacuo
  6. customThe crude product was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1e80b9e2c3b24ec284979ca967869979
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07557213B2

Notizen zur Reaktion

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