Water → HCID 59351245, compound

HRID 2191960Notes

Reaction equation

HRID 2191960 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[C:26]([Si:30]([CH3:48])([CH3:47])[O:31][CH:32]1[CH2:37][CH2:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][CH2:33]1)([CH3:29])([CH3:28])[CH3:27].C([O-])(=O)C.[K+].O>CC#N>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:35]3[CH2:36][CH2:37][CH:32]([O:31][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:47])[CH3:48])[CH2:33][CH:34]=3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 517044Potassium AcetateHCID 46207940(4-(3-chloropyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanoneHCID 53393368Tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)oxy)silane

Product 1

HCID 59351245HCID 59351245, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

1H-benzimidazol-2-yl(4-((3-chloro-2-pyrazinyl)oxy)phenyl)methanone (0.50 g, 1.4 mmol), tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-cyclohexen-1-yl)oxy)silane (0.68 g, 2.0 mmol), potassium acetate (1.0 g, 11.0 mmol), and bis[di-tert-butyl(phenyl)phosphane]dichloropalladium (0.066 g, 0.11 mmol) were taken up in 24 mL of 3:1 MeCN:water. The mixture was purged with nitrogen and heated to 100° C. After 18 hours, the mixture was diluted with 30 mL of water and extracted three times with 25 mL of 9:1 chloroform:isopropanol. The combined organic extracts were dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 25% EtOAc/hexanes) afforded 1H-benzimidazol-2-yl(4-((3-(4-((tert-butyl(dimethyl)silyl)oxy)-1-cyclohexen-1-yl)-2-pyrazinyl)oxy)phenyl)methanone.

Workup

  1. customThe mixture was purged with nitrogen
  2. additionthe mixture was diluted with 30 mL of water
  3. extractionextracted three times with 25 mL of 9:1 chloroform
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-600d6c2203ed46af9fb58a818e8c5c2b
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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