Sodium Carbonate → HCID 68181142, compound

HRID 2371247Notes

Reaction equation

HRID 2371247 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:19](=[O:36])[N:20]([C:27]2[O:35][C:31]3=[CH:32][CH:33]=[CH:34][C:30]3=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][C:39]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:19](=[O:36])[N:20]([C:27]2[O:35][C:31]3=[CH:32][CH:33]=[CH:34][C:30]3=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]2[CH:17]=[CH:16][C:15]([C:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH:39]=3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 38629021-Cyclohexenylboronic acidHCID 67486306HCID 67486306, compound

Product 1

HCID 68181142HCID 68181142, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-[2-(4-benzofuran-2yl-phenylcarbamoyl)-2-(4-bromo-phenyl)-ethyl]-benzoic acid methyl ester (0.4 g, 0.74 mmol), cyclohexen-2-ylboronic acid (0.23 g, 1.85 mmol), PdCl2 (o-tolylphosphine) (75 mg, 0.096 mmol), and Na2CO3 (390 mg, 3.70 mmol) in DME/EtOH/H2O (4:2:1) (17.5 mL) was heated in an oil bath at 130° C. for 2 h, cooled to rt, filtered and washed with EtOAc (20 mL). The solvent was removed under reduced pressure. The crude mixture was extracted with ethyl acetate (100 mL) and the organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel, eluting with ethyl acetate:hexanes (3:2) to afford 4-[2-(4-benzofuran-2-yl-phenylcarbamoyl)-2-(4-cyclohex-1-enyl-phenyl)-ethyl]-benzoic acid methyl ester as a white solid (0.42 g). 1H NMR (300 MHz, CDCl3): δ 10.23 (s, 1H), 7.81 (d, J=8.4 Hz, 2H), 7.54-7.65 (m, 4H), 7.21-7.34 (m, 8H), 6.10 (bt, 1H), 4.02 (m, 1H), 3.78 (s, 3H), 3.45 (dd, J=8.7, 13.5 Hz, 1H), 3.04 (dd, J=6.6, 13.5 Hz, 1H), 2.25-2.40 (m, 2H), 2.10-2.20 (m, 2H), 1.64-1.72 (m, 2H), 1.54-1.59 (m, 2H); LC-MS m/z=556 [C37H33NO4+H]+; TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate/hexanes (2:1); Rf=0.45.

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. washwashed with EtOAc (20 mL)
  4. customThe solvent was removed under reduced pressure
  5. extractionThe crude mixture was extracted with ethyl acetate (100 mL)
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude was purified by column chromatography on silica gel
  10. washeluting with ethyl acetate:hexanes (3:2)

Sources & evidence

ORD record
ord-d7bb5c0985ff405b91436faaa7321a22
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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