HCID 57708933, compound → HCID 57709030, compound

HRID 546868Notes

Reaction equation

HRID 546868 reaction equation
[CH2:1]([C:3]([C:26]1[CH:31]=[CH:30][C:29]([B:32]2[O:36][C:35]([CH3:38])([CH3:37])[C:34]([CH3:40])([CH3:39])[O:33]2)=[C:28]([CH3:41])[CH:27]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:25])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]>C(OCC)(=O)C.[C].[Pd]>[CH2:1]([C:3]([C:26]1[CH:31]=[CH:30][C:29]([B:32]2[O:33][C:34]([CH3:40])([CH3:39])[C:35]([CH3:37])([CH3:38])[O:36]2)=[C:28]([CH3:41])[CH:27]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2([O:20][Si:21]([CH3:23])([CH3:24])[CH3:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:25])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 57708933HCID 57708933, compound

Product 1

HCID 57709030HCID 57709030, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% palladium carbon (11.3 mg) was added to a solution of 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); 49.7 mg, 0.0867 mmol) in ethyl acetate (0.5 mL), and the mixture was stirred under hydrogen charging for three hours. The reaction mixture was filtered and concentrated to give the title compound (43.3 mg, 86%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-80b23814a11f47258e764d8c7cebf799
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…