Sodium Carbonate → HCID 117992415, compound

HRID 531125Notes

Reaction equation

HRID 531125 reaction equation
[CH2:1]([O:8][C:9]1[C:18](Br)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:20][CH2:21][CH3:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>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].C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:18]([CH:23]2[CH2:25][CH2:24]2)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:20][CH2:21][CH3:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117992246HCID 117992246, compound

Product 1

HCID 117992415HCID 117992415, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-(benzyloxy)-5-bromo-2-ethoxybenzoate (9.80 g), cyclopropylboronic acid (5.76 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (1.65 g), a 2 M aqueous sodium carbonate solution (40.2 mL), tris(dibenzylideneacetone)dipalladium(0) (1.72 g), and toluene (100 mL) was stirred overnight at 100° C. in an argon atmosphere. The reaction mixture was filtered, and then, the filtrate was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and then, 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 (8.76 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was poured to water
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  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-a948617692034cb1ae265b85cefea1a8
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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