Ammonium Chloride → HCID 57708987, compound

HRID 546908Notes

Reaction equation

HRID 546908 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:50][C:51]1[CH:52]=[C:53]([C:67]([C:72]2[CH:77]=[CH:76][C:75](/[CH:78]=[CH:79]/[C:80]([CH2:84][CH3:85])([OH:83])[CH2:81][CH3:82])=[C:74]([CH3:86])[CH:73]=2)([CH2:70][CH3:71])[CH2:68][CH3:69])[CH:54]=[C:55]([CH3:66])[C:56]=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:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:56]2[C:55]([CH3:66])=[CH:54][C:53]([C:67]([CH2:68][CH3:69])([C:72]3[CH:77]=[CH:76][C:75](/[CH:78]=[CH:79]/[C:80]([CH2:84][CH3:85])([OH:83])[CH2:81][CH3:82])=[C:74]([CH3:86])[CH:73]=3)[CH2:70][CH3:71])=[CH:52][C:51]=2[CH3:50])=[CH:7][CH:6]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57708978HCID 57708978, compound

Product 1

HCID 57708987HCID 57708987, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(4-Bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 34 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 (31.8 mg, 61%).

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-d22493e15fc14c67bcec3c4106c56173
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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