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 → HCID 57708996, compound

HRID 546863Notes

Reaction equation

HRID 546863 reaction equation
[CH2:1]([C:3]([C:25]1[CH:30]=[CH:29][C:28]([B:31]2[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]2)=[C:27]([CH3:40])[CH:26]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:24])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]>C(OCC)(=O)C.[C].[Pd]>[CH2:1]([C:3]([C:25]1[CH:30]=[CH:29][C:28]([B:31]2[O:32][C:33]([CH3:39])([CH3:38])[C:34]([CH3:36])([CH3:37])[O:35]2)=[C:27]([CH3:40])[CH:26]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:24])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 577089762-(4-{1-Ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 57708996HCID 57708996, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% palladium carbon (40 mg) was added to a solution of 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); 0.26 g, 0.48 mmol) in ethyl acetate (2.5 mL), and the mixture was stirred under hydrogen charging for three hours. The reaction mixture was filtered and concentrated to give the title compound (0.26 g, 100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f3d3352e3d3b459c8bbc1098f179f921
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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