Water → HCID 68688416, compound

HRID 1175211Notes

Reaction equation

HRID 1175211 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CC1(C)C(C)(C)OB([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH2:27])O1.C([O-])([O-])=O.[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:28]1([C:26]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH2:27])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 68689230HCID 68689230, compound

Product 1

HCID 68688416HCID 68688416, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 3-bromo-5-(pyridin-2-yl)benzoate (137 mg, 0.47 mmol), 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (162 mg, 0.70 mmol), Pd(PPh3)4 (19 mg, 0.023 mmol) and K2CO3 (195 mg, 1.41 mmol) were taken up in DME (5 mL) and water (1 mL) and heated to about 80° C. overnight. The reaction mixture was combined with water and the product was extracted into EtOAc (3×10 mL). The combined organic extracts were washed with water (1×10 mL), brine (1×10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified via automated flash chromatography (silica gel; 0 to 25% EtOAc in hexanes) to afford methyl 3-(1-phenylvinyl)-5-(pyridin-2-yl)benzoate. MS m/z=316 [M+1]+. Calc'd for C21H17NO2: 315.

Workup

  1. extractionthe product was extracted into EtOAc (3×10 mL)
  2. washThe combined organic extracts were washed with water (1×10 mL), brine (1×10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-7c44ea52a1824e0396215958e36c3e41
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

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