Cesium carbonate → HCID 67036178, compound

HRID 1623482Notes

Reaction equation

HRID 1623482 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[C:10]#[C:11][CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[CH:26]=1>CN(C=O)C>[CH3:22][O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[I:1])[C:9](=[O:15])[C:10]#[C:11][CH:12]([CH3:13])[CH3:14])[CH:26]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 67036292HCID 67036292, compound

Product 1

HCID 67036178HCID 67036178, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methyl-pent-2-ynoic acid (2-iodo-phenyl)-amide (21 g, 67.1 mmol) and cesium carbonate (33.0 g, 100.7 mmol) in DMF (170 ml) was stirred for 10 minutes. 3-bromomethyl-benzoic acid methyl ester (16.9 g, 73.8 mmol) was added. Then the mixture was stirred for 12 hours at room temperature. After removal of the 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)-(4-methyl-pent-2-ynoyl)-amino]-methyl}-benzoic acid methyl ester as yellow solid (15.9 g, 51%). MS calcd. for C21H20ClNO3 461.3, obsd. (ESI+) [(M+H)+] 461.9.

Workup

  1. stirringThen the mixture was stirred for 12 hours at room temperature
  2. customAfter removal of the 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-5b22e0df5ce245df9146ebd9e8f4ee33
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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