Ammonium Chloride → HCID 57709182, compound

HRID 547008Notes

Reaction equation

HRID 547008 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][C:6]=1[F:12].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:51][C:52]1[CH:53]=[C:54]([C:68]([C:73]2[CH:78]=[CH:77][C:76](/[CH:79]=[CH:80]/[C:81]([CH2:85][CH3:86])([OH:84])[CH2:82][CH3:83])=[C:75]([CH3:87])[CH:74]=2)([CH2:71][CH3:72])[CH2:69][CH3:70])[CH:55]=[C:56]([CH3:67])[C:57]=1B1OC(C)(C)C(C)(C)O1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:57]2[C:56]([CH3:67])=[CH:55][C:54]([C:68]([CH2:69][CH3:70])([C:73]3[CH:78]=[CH:77][C:76](/[CH:79]=[CH:80]/[C:81]([CH2:85][CH3:86])([OH:84])[CH2:82][CH3:83])=[C:75]([CH3:87])[CH:74]=3)[CH2:71][CH3:72])=[CH:53][C:52]=2[CH3:51])=[CH:7][C:6]=1[F:12]

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57443493Methyl 2-(4-chloro-2-fluorophenyl)acetateHCID 57708978HCID 57708978, compound

Product 1

HCID 57709182HCID 57709182, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(4-Chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 30 mg, 0.149 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (63 mg, 0.297 mmol) and water (0.2 mL) 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 toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for one hour. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with dichloromethane. 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 (32.5 mg, 60%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  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-7ae822ac315a4e09ad154a4a316c7931
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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