Potassium Carbonate → Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate

HRID 926151Notes

Reaction equation

HRID 926151 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:27])[C:8]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]2OS(C(F)(F)F)(=O)=O)=[CH:4][CH:3]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCO.O.CCOC(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:27])[C:8]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]2[C:32]2[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86691550Ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

Product 1

HCID 67126218Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (235 mg, 0.50 mmol) in PhCH3 (1.2 mL), EtOH (0.6 mL), H2O (0.6 mL) was added 4-chlorophenylboronic acid (86 mg, 0.55 mmol), K2CO3 (207 mg, 1.5 mmol), and PdCl2dppf (11 mg, 0.015 mmol). The reaction mixture was stirred at room temperature for 2 h and was then diluted with H2O and EtOAc. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give the titled compound and 37 mg of the bis-coupled product (ethyl 2-(1,7-bis(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate). 1H-NMR: 400 MHz, (CDCl3) δ: 7.60-7.72 (m, 4H), 7.45 (m, 2H), 7.23 (m, 2H), 3.93 (q, J=7 Hz, 2H), 2.48 (s, 3H), 1.13 (t, J=7 Hz, 3H).

Workup

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-ec73ccb1b87f45888fb0aac7c2f0e4d8
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

Loading…