Potassium Phosphate, Tribasic → HCID 57709128, compound

HRID 546969Notes

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:75]1[CH:80]=[CH:79][C:78](B2OC(C)(C)C(C)(C)O2)=[C:77]([CH3:90])[CH:76]=1)([C:56]1[CH:61]=[CH:60][C:59]([C:62]#[C:63][C:64]2([O:69][Si:70]([CH3:73])([CH3:72])[CH3:71])[CH2:68][CH2:67][CH2:66][CH2:65]2)=[C:58]([CH3:74])[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:78]2[CH:79]=[CH:80][C:75]([C:53]([CH2:54][CH3:55])([C:56]3[CH:61]=[CH:60][C:59]([C:62]#[C:63][C:64]4([O:69][Si:70]([CH3:72])([CH3:73])[CH3:71])[CH2:68][CH2:67][CH2:66][CH2:65]4)=[C:58]([CH3:74])[CH:57]=3)[CH2:51][CH3:52])=[CH:76][C:77]=2[CH3:90])=[CH:44][C:43]=1[F:49]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of palladium acetate (3.4 mg, 0.015 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (12.3 mg, 0.03 mmol) and potassium phosphate (63.7 mg, 0.3 mmol) in water (0.045 mL) and toluene (0.200 mL) was stirred for three minutes. A solution of (4-chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 32.6 mg, 0.16 mmol) and 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 32-(4); 60.0 mg, 0.10 mmol) in toluene (0.25 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 (52.6 mg, 81%).

Workup

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

Sources & evidence

ORD record: ord-4e18c5c0d82e4c7cb7f50e0f002edada
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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