Water → Methyl 2-hydroxy-3-(3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoyl)benzoate

HRID 876542Notes

Reaction equation

HRID 876542 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.[C:14]([C:17]1[C:18]([OH:27])=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21])(=[O:16])[CH3:15].C1CCN2C(=NCCC2)CC1.O>N1C=CC=CC=1>[OH:27][C:18]1[C:17]([C:14](=[O:16])[CH2:15][C:9](=[O:10])[C:8]2[C:3]([C:2]([F:13])([F:12])[F:1])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13037297Methyl 3-acetyl-2-hydroxybenzoateHCID 450819512-(Trifluoromethyl)nicotinoyl chloride

Product 1

HCID 58477324Methyl 2-hydroxy-3-(3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoyl)benzoateYield 111.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

2-(trifluoromethyl)pyridine-3-carbonyl chloride 25 (300 mg, 1.46 mmol) was added to a mixture of methyl 3-acetyl-2-hydroxybenzoate 38 (183 mg, 1.46 mmol) and DBU (446 mg, 2.92 mmol) in pyridine at 0° C. The reaction mixture was heated at 80° C. for 12 h. The resulting mixture was poured into H2O and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated to give 39 (600 mg) which was used with no further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d08636f33b3248f983e03ed7ac4fe129
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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