Dimethylformamide → 5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine

HRID 40721

Reaktionsgleichung

Reaktionsgleichung von HRID 40721
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]([OH:19])=O)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.F[C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[C:25]([F:30])[N:24]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.N1C=CC=CC=1>[F:30][C:25]1[N:24]=[C:23]2[O:19][C:17]([C:15]3[CH:16]=[C:11]4[CH:10]=[CH:9][N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][CH:20]=5)[C:12]4=[N:13][CH:14]=3)=[N:29][C:28]2=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 450800062,6-Difluoropyridin-3-amineHCID 582201621-(4-Methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

Produkt 1

HCID 582201575-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a stirred solution of 1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (47 mg, 0.17 mmol) in CH2Cl2 (2 mL) was added 1-chloro-N,N-2-trimethylpropenylamine (45 μL, 0.34 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6-difluoro-pyridin-3-ylamine (20 mg, 0.15 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue, to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150° C. for 10 min, after which the resulting mixture was filtered and concentrated, affording 5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine as a crude residue which was subsequently used without further purification. ES MS (M+H+)=375.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customaffording a residue that
  3. additionwas added in one portion
  4. concentrationAfter an additional 30 minutes the reaction mixture was concentrated to dryness
  5. customaffording a residue
  6. filtrationafter which the resulting mixture was filtered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-36b9a2fd13594de196727a03f2237ade
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530483B2

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