Cesium carbonate → HCID 58201660, compound

HRID 1623477Notes

Reaction equation

HRID 1623477 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:13])[C:10]#[C:11][CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1>CN(C=O)C>[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[I:1])[C:9](=[O:13])[C:10]#[C:11][CH3:12])[CH:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 23250757HCID 23250757, compound

Product 1

HCID 58201660HCID 58201660, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of but-2-ynoic acid (2-iodo-phenyl)-amide (2.85 g, 10 mmol) and cesium carbonate (4.89 g, 15 mmol) in DMF (20 ml) was stirred for 10 minutes. 3-bromomethyl-benzoic acid methyl ester (2.52 g, 11 mmol) was added. Then the mixture was stirred for 12 hours at room temperature. After removal of solids, the filtrate was treated with water and extracted with ether. The organic layer was dried over sodium sulfate and concentrated to give the residue which was purified by flash chromatography, eluting with ethyl acetate/hexane=1:4 to afford the product 3-{[(2-iodo-phenyl)-(1-oxo-but-2-ynyl)-amino]-methyl}-benzoic acid methyl ester as yellow solid (3.03, 70%). MS calcd. for C19H16INO3 433.3, obsd. (ESI+) [(M+H)+] 434.1.

Workup

  1. stirringThen the mixture was stirred for 12 hours at room temperature
  2. customAfter removal of solids
  3. additionthe filtrate was treated with water
  4. extractionextracted with ether
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give the residue which
  8. customwas purified by flash chromatography
  9. washeluting with ethyl acetate/hexane=1:4

Sources & evidence

ORD record
ord-3a578299231544fba51369e9086f0812
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

Loading…