Potassium Phosphate, Tribasic → HCID 57709015, compound

HRID 547125Notes

Reaction equation

[C:1]([Si:5]([O:8][CH:9]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH2:41][CH3:42])([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[C:27]([CH3:40])[CH:26]=2)[CH2:23][CH3:24])=[CH:18][C:17]=1[CH3:43])[C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:44][O:45][C:46](=[O:63])[C@@H:47]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C:48]1[CH:53]=[CH:52][C:51](Cl)=[CH:50][CH:49]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:44][O:45][C:46](=[O:63])[C@@H:47]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C:48]1[CH:53]=[CH:52][C:51]([C:28]2[CH:29]=[CH:30][C:25]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:17]([CH3:43])[CH:18]=3)([CH2:23][CH3:24])[CH2:41][CH3:42])=[CH:26][C:27]=2[CH3:40])=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Toluene (2.0 mL) and water (0.20 mL) were added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 23-(1); 50.0 mg, 0.0824 mmol), (S)-t-butoxycarbonylamino-(4-chloro-phenyl)-acetic acid methyl ester (Example 166-(1); 37.0 mg, 0.123 mmol), palladium (II) acetate (1.9 mg, 0.00846 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (6.8 mg, 0.0166 mmol) and potassium phosphate (52.0 mg, 0.245 mmol). After replacement with nitrogen, the mixture was stirred with microwave heating at 150° C. for five minutes. The reaction mixture was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 70:30) to give the target compound as a colorless oil (56.4 mg, 92%).

Workup

customThe reaction mixture was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record: ord-c46b4512dcb0438eb279d2835be2d9ad
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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