Potassium Phosphate, Tribasic → [4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-acetic Acid Methyl Ester

HRID 546929Notes

Reaction equation

HRID 546929 reaction equation
[C:1]([Si:5]([CH3:43])([CH3:42])[O:6][CH:7]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[C:23]([CH3:36])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:37])([CH3:4])([CH3:3])[CH3:2].[CH3:44][O:45][C:46](=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[C:50](Br)[CH:49]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[CH3:44][O:45][C:46](=[O:55])[CH2:47][C:48]1[CH:49]=[C:50]([C:24]2[CH:25]=[CH:26][C:21]([C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:42])[CH3:43])[C:38]([CH3:41])([CH3:40])[CH3:39])=[C:11]([CH3:37])[CH:12]=3)([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:22][C:23]=2[CH3:36])[CH:51]=[CH:52][CH:53]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 577089262-[4-(1-{4-[3-(t-Butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 57708909[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-acetic Acid Methyl EsterYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

N,N-Dimethylformamide (0.7 mL) was added to 2-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 24-(1); 70 mg, 0.116 mmol), (3-bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 53 mg, 0.232 mmol), tetrakis(triphenylphosphine)palladium (0) (26.8 mg, 0.023 mmol) and potassium phosphate (63.9 mg, 0.30 mmol). The mixture was stirred with microwave heating at 140° C. for seven minutes in a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=10/1) to give the title compound (36 mg, 50%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by preparative TLC (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-c3d6759dc6bb426da55863df54b56bc9
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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