Diisopropylethylamine → Methyl 2-(trifluoromethyl)isonicotinate

HRID 57734

Reaktionsgleichung

Reaktionsgleichung von HRID 57734
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([OH:8])=[O:7].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:24]=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl.CO>[CH3:24][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][N:11]=[C:3]([C:2]([F:12])([F:1])[F:13])[CH:4]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 147614472-(Trifluoromethyl)pyridine-4-carboxylic acid

Produkt 1

HCID 46311185Methyl 2-(trifluoromethyl)isonicotinateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under inert atmosphere, a mixture of 2-Trifluoromethyl-isonicotinic acid (1.0 equiv.), BOP (1.2 equiv.), DIPEA (1.5 equiv.) in DCM (C=0.1 molL−1) and MeOH (C=0.1 molL−1) was stirred at RT for 16 h. The reaction mixture was evaporated to dryness. The resulting residue was hydrolysed with HCl 1N and extracted twice with Et2O. The organic layers were combined, washed with a saturated solution of NaHCO3, brine, dried over MgSO4, concentrated to afford the product as transparent oil in a 66% yield.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. extractionextracted twice with Et2O
  3. washwashed with a saturated solution of NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-180c3ee89f924bc4b096cdf8b794aa59
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434734B2

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