Cesium carbonate → HCID 68425331, compound

HRID 1992799Notes

Reaction equation

HRID 1992799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:17]([O:16][C:14]([C:12]1[N:11]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][N:24]=2)[N:10]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:13]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 127522376-Bromomethyl-nicotinic acid methyl esterHCID 86614809HCID 86614809, compound

Product 1

HCID 68425331HCID 68425331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the intermediate from step C (522 mg, 1.66 mmol) in DMF (10 mL) was added the intermediate from step D (460 mg, 2.0 mmol), followed by cesium carbonate (815 mg, 2.5 mmol). After stirring the reaction at room temperature for 3 hours, it was quenched by adding water and extracting with ethyl acetate (3×). The organic layer was washed with brine and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 30% ethyl acetate-hexanes. 1H NMR (CDCl3, 500 MHz): 9.21 (d, J=2.1 Hz, 1H), 8.25 (dd, J=2.2, 8.2 Hz, 1H), 7.97 (d, J=1.8 Hz, 1H), 7.69 (dd, J=2.1, 8.3 Hz, 1H), 7.5 (d, J=8.2 Hz, 1H), 7.18 (s, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.01 (s, 2H), 3.97 (s, 3H), 1.53 (s, 9H). LC-MS: 2.87 min; (M+H−56)=406.0.

Workup

  1. customthe reaction at room temperature for 3 hours
  2. customit was quenched
  3. additionby adding water
  4. extractionextracting with ethyl acetate (3×)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. custom2.87 min

Sources & evidence

ORD record
ord-e1b26ea730d84f4297089cf37f78596a
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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