Cesium carbonate → HCID 58746171, compound

HRID 724258Notes

Reaction equation

HRID 724258 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1Cl.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:18][S:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1>C1(C)C=CC=CC=1.CN1CCCC1=O.O.C(OCC)(=O)C.[Cu](I)I>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[O:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:19][CH3:18])[CH:21]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 819931Methyl 2-chloronicotinateHCID 99204073-(Methylsulfanyl)phenol

Product 1

HCID 58746171HCID 58746171, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21877177toluene N-methylpyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloronicotinic acid methyl ester (WO 02/085358, pg. 21, example 1) (8.00 g, 47 mmol), caesium carbonate (21.30 g, 65 mmol) and copper iodide (890 mg, 4.7 mmol) were dissolved in a toluene:1-methyl-2-pyrrolidinone 4:1 mixture (155 mL) and the reaction mixture treated with 3-methylsulphanyl-phenol (6.21 g, 44 mmol) (WO 98/45268, pg. 68, preparation 61). The reaction mixture was heated td 110° C. for 18 hours. The reaction mixture was diluted with water (250 mL), and ethyl acetate (250 mL) and filtered through Arbocel®. The organic layer was separated and the aqueous extracted with ethyl acetate (2×250 mL). The organics were combined, washed with water and brine and dried over magnesium sulphate. The organics were concentrated in vacuo and the residue purified by column chromatography on silica gel eluting with toluene:ethyl acetate 100:0 to 98:2. The crude product was triturated with hexane:ether 66:33 to yield the title product, 4.90 g.

Workup

  1. custom68, preparation 61)
  2. filtrationfiltered through Arbocel®
  3. customThe organic layer was separated
  4. extractionthe aqueous extracted with ethyl acetate (2×250 mL)
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationThe organics were concentrated in vacuo
  8. customthe residue purified by column chromatography on silica gel eluting with toluene:ethyl acetate 100:0 to 98:2
  9. customThe crude product was triturated with hexane:ether 66:33

Sources & evidence

ORD record
ord-cf696ea81b5f4a598dd8d4d1e0f273b7
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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