Diisopropylethylamine → Methyl 2-(trifluoromethyl)isonicotinate

HRID 57734

Reaction equation

HRID 57734 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 46311185Methyl 2-(trifluoromethyl)isonicotinateYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-180c3ee89f924bc4b096cdf8b794aa59
Source dataset
uspto-grants-2016_09
Patent number
US09434734B2

Linked notes

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