4-Methylmorpholine → N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide

HRID 931388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931388
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[C:17]([C:19]([OH:21])=O)[O:16][C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1.[Br:24][C:25]1[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.CN(C)C(Cl)=[N+](C)C>CN(C=O)C>[Br:24][C:25]1[C:26]([NH:31][C:19]([C:17]2[O:16][C:13]3=[N:14][CH:15]=[C:10]([CH2:9][O:8][CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=4)[CH:11]=[C:12]3[CH:18]=2)=[O:21])=[N:27][CH:28]=[CH:29][CH:30]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 8177002-Amino-3-bromopyridineHCID 10989639Chloro-N,N,N',N'-tetramethylformamidinium HexafluorophosphateHCID 900505445-(((4-Methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid

Produkt 1

HCID 90050548N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

In an oven-dried sealed tube, a mixture of 5-(((4-methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid (2.0 g, 6.4 mmol), 3-bromo-2-amino pyridine (3.31 g, 19.2 mmol), N-methyl morpholine (1.93 g, 19.2 mmol) and N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (3.58 g, 12.8 mmol) in DMF (20 mL) was heated to 70° C. for 5 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether to give the title compound. MS: m/z=468.5 (M+1).

Aufarbeitung

  1. customIn an oven-dried sealed tube
  2. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-2cdc9a834ef840699759a548ccfcb69e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296750B2

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