Potassium Carbonate → Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoate

HRID 512925Notes

Reaction equation

HRID 512925 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]4[CH2:22][O:21]4)[CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(#N)C>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32][CH2:22][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14](/[CH:13]=[CH:12]/[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[OH:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 867207317-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinoline

Product 1

HCID 86720738Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoateYield 31.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of epoxide 30 (37 g, 0.120 mol) in a mixture of dimethylformamide (140 ml) and acetonitrile (200 ml) was added methyl-2-mercaptobenzoate (20.0 g, 0.145 mol), followed by addition of anhydrous potassium carbonate (19.8 g, 0.145 mol). The reaction mixture was stirred overnight, filtered and concentrated. The resulting mixture was poured into water (2.0 L), stirred and extracted with ethylacetate (1.0 L). The organic layer was washed with water (500 ml) and brine (500 ml), dried over anhydrous sodium sulphate, evaporated and subjected to FC (EtOAc/hexanes) to afford product as a pale yellow solid 46 (18.0 g, 31% yield).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe resulting mixture was poured into water (2.0 L)
  4. stirringstirred
  5. extractionextracted with ethylacetate (1.0 L)
  6. washThe organic layer was washed with water (500 ml) and brine (500 ml)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-13a21cd34a534b759ff8f3a5b13453a5
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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