Sodium Carbonate → HCID 90422895, compound

HRID 2272453Notes

Reaction equation

HRID 2272453 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:13]([O:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:34][CH2:33][CH2:32]2)[C:28](Br)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:13]([O:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:34][CH2:33][CH2:32]2)[C:28]([CH:1]2[CH2:3][CH2:2]2)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90422969HCID 90422969, compound

Product 1

HCID 90422895HCID 90422895, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Cyclopropylboronic acid (6.18 g) and sodium carbonate (15.3 g) were added to a mixed solution of methyl 2-(benzyloxy)-5-bromo-4-cyclobutylbenzoate (13.5 g) in toluene (240 mL) and water (60 mL), and the mixture was deaerated for 20 minutes in an argon stream. Then, tris(dibenzylideneacetone)dipalladium(0) (6.25 g) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (2.80 g) were added thereto, and the mixture was further deaerated for 5 minutes. The reaction mixture was stirred at 100 C for 16 hours. The reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. Combined organic layers were washed with water and saturated saline in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (8.5 g).

Workup

  1. waitthe mixture was further deaerated for 5 minutes
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite was washed with ethyl acetate
  4. washCombined organic layers were washed with water and saturated saline in this order
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fb992a5c0c4d4458808a3ba812a2723a
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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