Sodium Carbonate → HCID 15461786, compound

HRID 566435Notes

Reaction equation

HRID 566435 reaction equation
Br[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][O:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:16][O:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 15402632Boronic acid, [4-methoxy-2-(methoxymethoxy)phenyl]-HCID 15461785HCID 15461785, compound

Product 1

HCID 15461786HCID 15461786, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of ethyl 5-bromo-1-n-butyl-1H-imidazole-4-carboxylate (0,10 g, 0.37 mmol), 2-methoxymethoxy-4methoxyphenylboronic acid (0.16 g, 0.73 mmol), sodium carbonate (0.08 g, 0.73 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.04 g) in 12 mL of toluene/ethanol/water (10/1/1) was stirred at reflux for 24 h. After an aqueous work up, extracting with ethyl acetate (3×20 mL), the combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash column chromatography (1:1 ethyl acetate/hexane) of the residue afforded the title compound as an oil (0.06 g, 46%). 1H NMR (250 MHz, CDCl3) δ 7.53 (s, 1H), 7.09 (d, 1H), 6.75 (d, 1H), 6.60 (dd, 1H), 5.05 (q, 2H), 4.21 (q, 2H), 3.85 (s, 3H) 3.80 (t, 2H), 3.30 (s, 3H) 1.60 (quintet, 2H), 1.30 (m, 5H), 0.80 (t, 3H).

Workup

  1. temperatureat reflux for 24 h
  2. extractionAfter an aqueous work up, extracting with ethyl acetate (3×20 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customAfter removing the solvent under reduced pressure, flash column chromatography (1:1 ethyl acetate/hexane) of the residue

Sources & evidence

ORD record
ord-a8164e134658438a854d311e7db82e77
Source dataset
uspto-grants-2001_01
Patent number
US06174906B1

Reaction notes

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