Water → HCID 70080165, compound

HRID 843991Notes

Reaction equation

HRID 843991 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.O>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[O:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([I:24])[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 122723-IodophenolHCID 2111911benzyl 2-chloropyridine-3-carboxylate

Product 1

HCID 70080165HCID 70080165, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution 2-Chloro-nicotinic acid benzyl ester (1.7 grams, 6.86 mmole), cesium carbonate (4.5 grams, 13.7 mmole) and 3-iodophenol (1.7 grams, 7.54 mmole) in dimethylformamide (20 ml) was stirred for 2 hours at 70-80° C. The mixture was poured into 150 ml water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to an oil which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent (2.32 g). MW 431.24; MS (m/e) 432 (M++1).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil which
  6. customwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent (2.32 g)

Sources & evidence

ORD record
ord-26afa9a1c1ff4ad6872d57f7cddb1ae7
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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