Water → N-(5-(furan-2-yl)-4-methylthiazol-2-yl)acetamide

HRID 2386178Notes

Reaction equation

HRID 2386178 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].[C:12](=O)([O-])[O-].[Na+].[Na+].O.CO[CH2:21][CH2:22][O:23][CH3:24]>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>[O:23]1[CH:24]=[CH:12][CH:21]=[C:22]1[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 822437N-(5-bromo-4-methyl-1,3-thiazol-2-yl)acetamide

Product 1

HCID 59362180N-(5-(furan-2-yl)-4-methylthiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
95 °C

Procedure

A mixture of N-(5-bromo-4-methylthiazol-2-yl)acetamide (4 g), furan-2-yl-2-boronic acid (4.22 g), tetrakis(triphenylphosphine)palladium (1.8 g) and 2 N sodium carbonate (36 ml) in DME (60 ml) was stirred at 95° C. for 18 h. After cooling, water (100 ml) was added. Extraction with ethyl acetate (3×80 ml), drying, concentration and purification (SiO2, 0 to 100% ethyl acetate in hexane) gave pure N-(5-(furan-2-yl)-4-methylthiazol-2-yl)acetamide (2.95 g).

Workup

  1. temperatureAfter cooling
  2. extractionExtraction with ethyl acetate (3×80 ml)
  3. customdrying
  4. concentrationconcentration and purification (SiO2, 0 to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ed6612c653dd4662aa8033b0eedf27e3
Source dataset
uspto-grants-2012_09
Patent number
US08268818B2

Reaction notes

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