Potassium Phosphate, Tribasic → HCID 57709058, compound

HRID 546977Notes

Reaction equation

HRID 546977 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:38][O:39][C:40](=[O:50])[CH2:41][C:42]1[CH:47]=[CH:46][C:45](Cl)=[CH:44][C:43]=1[F:49].[CH2:51]([C:53]([C:76]1[CH:81]=[CH:80][C:79](B2OC(C)(C)C(C)(C)O2)=[C:78]([CH3:91])[CH:77]=1)([C:56]1[CH:61]=[CH:60][C:59]([C:62]#[C:63][C:64]2([O:70][Si:71]([CH3:74])([CH3:73])[CH3:72])[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]2)=[C:58]([CH3:75])[CH:57]=1)[CH2:54][CH3:55])[CH3:52]>O.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][O:39][C:40](=[O:50])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:79]2[CH:80]=[CH:81][C:76]([C:53]([CH2:54][CH3:55])([C:56]3[CH:61]=[CH:60][C:59]([C:62]#[C:63][C:64]4([O:70][Si:71]([CH3:73])([CH3:74])[CH3:72])[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]4)=[C:58]([CH3:75])[CH:57]=3)[CH2:51][CH3:52])=[CH:77][C:78]=2[CH3:91])=[CH:44][C:43]=1[F:49]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57443493Methyl 2-(4-chloro-2-fluorophenyl)acetateHCID 57708933HCID 57708933, compound

Product 1

HCID 57709058HCID 57709058, compoundYield 77.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of palladium acetate (2.0 mg, 0.009 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (7.4 mg, 0.018 mmol) and potassium phosphate (38.4 mg, 0.181 mmol) in water (0.032 mL) and toluene (0.150 mL) was stirred for three minutes. A solution of (4-chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 19.6 mg, 0.097 mmol) and 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclohexylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 35-(4); 37.1 mg, 0.0647 mmol) in toluene (0.18 mL) was added, and the mixture was stirred in a nitrogen atmosphere at 100° C. for one hour. After filtration through cotton plug, the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (3% ethyl acetate/hexane) to give the title compound (30.9 mg, 77%).

Workup

  1. filtrationAfter filtration through cotton plug
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by thin layer silica gel chromatography (3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3b7d55cac81840fcbb33dd5749b9611a
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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