Sodium Carbonate → HCID 23594025, compound

HRID 1612058Notes

Reaction equation

HRID 1612058 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:15][O:16][C:17]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][O:16][C:17]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[CH:20]=[CH:19][C:18]=1[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10751184Methyl 2-chloro-3-nitrobenzoateHCID 22252933HCID 22252933, compound

Product 1

HCID 23594025HCID 23594025, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-3-nitrobenzoic acid, methyl ester, (2.06 g, 9.61 mM), 1-methoxy-5,6,7,8-tetrahydronaphthalene-2-boronic acid, (2.08 g, 10.09 mM), tetrakis(triphenylphosphine)palladium(0) (0.583 g, 0.5 mM), and 2M aqueous sodium carbonate solution (10.5 mL, 21.0 mM) in THF (50 mL) was stirred at reflux for 48 hours in the absence of light. The mixture was cooled to room temperature, the THF removed in vacuo, and the resulting aqueous residue dissolved in ethyl acetate and brine. The solvent layers were separated, the aqueous layer extracted with ethyl acetate (4×25 mL), the combined ethyl acetate extracts washed successively with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant black oil was purified by column chromatography on silica gel (elution with 5–15% ethyl acetate/hexane) to afford 0.656 g (20%) of the title compound 2-(1-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-nitrobenzoic acid, methyl ester as a yellow solid (MW 341.37, C19H19NO5).

Workup

  1. temperatureat reflux for 48 hours in the absence of light
  2. customthe THF removed in vacuo
  3. dissolutionthe resulting aqueous residue dissolved in ethyl acetate
  4. customThe solvent layers were separated
  5. extractionthe aqueous layer extracted with ethyl acetate (4×25 mL)
  6. washthe combined ethyl acetate extracts washed successively with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resultant black oil was purified by column chromatography on silica gel (elution with 5–15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b6e1b2cdac2c4d58813a33e6f7522965
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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