Ethyl Acetate → HCID 57709057, compound

HRID 547010Notes

Reaction equation

HRID 547010 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N:8][C:9](Cl)=[CH:10][CH:11]=1)[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:22][C:23]1[CH:24]=[C:25]([C:39]([C:44]2[CH:49]=[CH:48][C:47](/[CH:50]=[CH:51]/[C:52]([CH2:56][CH3:57])([OH:55])[CH2:53][CH3:54])=[C:46]([CH3:58])[CH:45]=2)([CH2:42][CH3:43])[CH2:40][CH3:41])[CH:26]=[C:27]([CH3:38])[C:28]=1B1OC(C)(C)C(C)(C)O1.C(OCC)(=O)C>CN(C)C=O.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>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([C:28]2[C:27]([CH3:38])=[CH:26][C:25]([C:39]([CH2:40][CH3:41])([C:44]3[CH:49]=[CH:48][C:47](/[CH:50]=[CH:51]/[C:52]([CH2:56][CH3:57])([OH:55])[CH2:53][CH3:54])=[C:46]([CH3:58])[CH:45]=3)[CH2:42][CH3:43])=[CH:24][C:23]=2[CH3:22])=[CH:10][CH:11]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 15661146Ethyl 2-(6-chloropyridin-3-yl)acetateHCID 57708978HCID 57708978, compound

Product 1

HCID 57709057HCID 57709057, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

(6-Chloro-pyridin-3-yl)-acetic acid ethyl ester (30 mg, 0.149 mmol), tetrakis(triphenylphosphine)palladium (0) (16 mg, 0.014 mmol) and potassium phosphate (32 mg, 0.149 mmol) were added to a solution of (E)-1-(4-{1-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-3-ethyl-1-penten-3-ol (Example 38-(6); 50 mg, 0.099 mmol) in N,N-dimethylformamide (0.5 mL). After replacement with nitrogen, the mixture was stirred with microwave heating at 140° C. for 10 minutes. Then, ethyl acetate was added to the reaction mixture, which was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the target compound as a colorless oil (11.6 mg, 22%).

Workup

  1. washwas washed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a0a75954c04b471e9a18b54ea9c48b2d
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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