Sodium hydride → 4-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester

HRID 453062

Reaktionsgleichung

Reaktionsgleichung von HRID 453062
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17](F)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1>C1COCC1>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=2)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3464554-Amino-2-bromopyridineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Produkt 1

HCID 866585844-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl esterAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Bromo-pyridin-4-ylamine 2 (4.3 g; 25 mmol) and NaH 60% (1.5 g; 37 mmol) was at 0° C. stirred for 1 h in dry THF (50 ml) and then a solution of 4-Fluoro-3-nitro-benzoic acid methyl ester 1 (5 g; 25 mmol) in dry THF (50 ml) was addeddrop. The resulting cold solution was allowed to reach RT and stirred overnight for completion of the reaction. LCMS showed complete conversion to product and the reaction was quenched by addition of iPrOH and H2O. A precipitate was formed and this was filtered off, dried under educed pressure to obtain 3 as a yellow solid (7.5 g). Yield 85%. The product identity was confirmed by NMR and LCMS and taken for the next step.

Aufarbeitung

  1. customwas at 0° C.
  2. customto reach RT
  3. customthe reaction was quenched by addition of iPrOH and H2O
  4. customA precipitate was formed
  5. filtrationthis was filtered off
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-01736928d2b048e1b0e4f8a8a2b11764
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492408B2

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