Dimethylformamide → 5-Bromo-N-cyclopropylpyridine-2-carboxamide

HRID 557882

Reaktionsgleichung

Reaktionsgleichung von HRID 557882
C([N:4](CC)[CH:5]([CH3:7])[CH3:6])(C)C.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=1.C1(N)CC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O>C(OCC)(=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:4][CH:5]2[CH2:7][CH2:6]2)=[O:19])=[N:15][CH:16]=1

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6085445-Bromopyridine-2-carboxylic acid

Produkt 1

HCID 263700895-Bromo-N-cyclopropylpyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N,N-Diisopropylethylamine (0.69 mL, 0.0040 mol) was added to a mixture of 5-bromopyridine-2-carboxylic acid (400 mg, 0.002 mol), cyclopropylamine (0.16 mL, 0.0024 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 0.0024 mol) in N,N-dimethylformamide (9.4 mL, 0.12 mol) at 0° C. and the mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried over sodium sulfate, filtered and concentrated. The product was purified by CombiFlash eluting with CH2Cl2/EtOAc (max.EtOAc 20%). LC-MS: 241.1/243.1 (M+H+)

Aufarbeitung

  1. washwashed with water and brine successively
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by CombiFlash
  6. washeluting with CH2Cl2/EtOAc (max.EtOAc 20%)

Quellen und Nachweise

ORD-Eintrag
ord-608f3976613242cc85a4cb23aedc7b10
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058288B2

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