Sodium Carbonate → HCID 117992144, compound

HRID 531063Notes

Reaction equation

HRID 531063 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10][C:9]=2[O:27][CH:28]([CH3:30])[CH3:29])=[CH:4][CH:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]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>[CH:31]1([C:13]2[CH:12]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:10]=[C:9]([O:27][CH:28]([CH3:29])[CH3:30])[C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:33][CH2:32]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117992336HCID 117992336, compound

Product 1

HCID 117992144HCID 117992144, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of ethyl 4′-fluoro-2-isopropoxy-6-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-carboxylate (1.67 g), cyclopropylboronic acid (0.955 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (228 mg), a 2 M aqueous sodium carbonate solution (5.56 mL), tris(dibenzylideneacetone)dipalladium(0) (238 mg), and toluene (15 mL) was stirred at 100° C. for 2 hours 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 (1.22 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-a4a46f91f4894cbeaf72fcae62431d5c
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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