Cesium carbonate → HCID 57595415, compound

HRID 1786024Notes

Reaction equation

HRID 1786024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:39][C:40]1[CH:41]=[C:42]([CH:47]=[CH:48][CH:49]=1)[C:43]([O:45][CH3:46])=[O:44]>CN(C=O)C>[CH3:46][O:45][C:43](=[O:44])[C:42]1[CH:47]=[CH:48][CH:49]=[C:40]([CH2:39][O:29][C:26]2[CH:25]=[CH:24][C:23]([C:22]([N:15]3[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@H:12]([N:8]([C:9](=[O:11])[CH3:10])[C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:13][C@@H:14]3[CH3:31])=[O:30])=[CH:28][CH:27]=2)[CH:41]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 57595415HCID 57595415, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (150 mg, 0.35 mmol) was dissolved in DMF (5 mL) at room temperature. Cs2CO3 (283 mg, 0.87 mmol) was added followed by methyl 3-(bromomethyl)benzoate (119 mg, 0.52 mmol) and the reaction was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and dissolved in ethyl acetate (15 mL). The reaction mixture was washed with sat. aq. NaHCO3 (15 mL), water (15 mL) and brine (15 mL). The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (5/95 ethyl acetate/hexane-50/50 ethyl acetate/hexane gradient) to afford slightly yellow solid product (111 mg, 54%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate (15 mL)
  3. washThe reaction mixture was washed with sat. aq. NaHCO3 (15 mL), water (15 mL) and brine (15 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography (5/95 ethyl acetate/hexane-50/50 ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-3fa66ee1848241f38ef8c6c545005537
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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