Ethyl Acetate → 3-(5-Isopropyl-thiazol-4-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

HRID 1888922Notes

Reaction equation

HRID 1888922 reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[CH:7]([CH3:9])[CH3:8].[C:10](=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18](=[O:41])[C:19]1C=C(B2OC(C)(C)C(C)(C)O2)C=[C:21]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=2)[CH:20]=1.CCO[C:45]([CH3:47])=O>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][O:17][C:18](=[O:41])[C:19]1[CH:20]=[C:21]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=2)[CH:9]=[C:7]([C:3]2[N:4]=[CH:5][S:6][C:2]=2[CH:45]([CH3:47])[CH3:10])[CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 594325365-Bromo-4-isopropylthiazoleHCID 59432564Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 594325573-(5-Isopropyl-thiazol-4-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-4-isopropyl-thiazole (0.131 g. 1 mmol), Pd(PPh3)4 (56 mg, 0.05 mmol) and potassium carbonate (0.196 g, 1 mmol) in DME/H2O (5 ml/2 ml) was added 3-(5-methyl-pyridin-2-yl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.250 g, 1 mmol) under N2 atmosphere. The reaction mixture was heated to 80° C. for three hours, then cooled and stirred at room temperature for 18 hours. The reaction mixture was poured into EtOAc, and the organic phase was separated, washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (15% EtOAc in hexanes) to give 85 mg of 3-(5-Isopropyl-thiazol-4-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester.

Workup

  1. temperaturecooled
  2. customthe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. temperatureThe reaction mixture was cooled
  8. customsolvent was evaporated under reduced pressure
  9. customThe residue was purified by flash-chromatography (15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-656ed711e7964cda91e5351dca778e24
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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