Ethanol → 4-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

HRID 2091700Notes

Reaction equation

HRID 2091700 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>COCCOC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8]

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 592500134-Chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

Product 1

HCID 592500334-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrileYield 15.2%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile (0.200 g, 0.871 mmol), 2,4-dichlorophenylboronic acid (0.249 g, 1.31 mmol), bis(triphenylphosphine)palladium dichloride (0.061 g, 0.0871 mmol), sodium carbonate (0.184 g, 1.74 mmol) were taken up in DME (3 mL), ethanol (1 mL) and water (1 mL) and microwaved at 125° for 30 minutes. Mixture was diluted with ethyl acetate (10 mL) and extracted. The organic phase was dried with sodium sulfate, filtered and evaporated. ISCO purification on silica gel using 10% ethyl acetate in hexane to 50% ethyl acetate in hexane afforded the title compound (45 mg, 15%). LCMS: (FA) ES+, 340. 1H NMR (400 MHz, d6-DMSO) δ: 7.44 (d, 1H), 7.20-7.17 (m, 2H), 3.43-3.28 (m, 4H), 3.16-2.93 (m, 4H).

Workup

  1. extractionextracted
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customISCO purification on silica gel using 10% ethyl acetate in hexane to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-37e5806bf87046549cbf629a9c7fe705
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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