Cesium carbonate → HCID 57719127, compound

HRID 1985121Notes

Reaction equation

HRID 1985121 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20](I)[CH:19]=3)[N:12]([CH3:27])[C:11]2=[O:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:31]B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH3:31])[CH:19]=3)[N:12]([CH3:27])[C:11]2=[O:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 139377Methylboronic AcidHCID 57719296HCID 57719296, compound

Product 1

HCID 57719127HCID 57719127, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-tert-Butyl-benzyl)-4-[3-(3-iodo-4-methoxy-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.300 g, 0.580 mmole), methyl boronic acid (0.069 g, 1.16 mmole) and cesium carbonate (0.264 g, 1.74 mmole) are mixed in dioxane (6.0 mL). After bubbling with nitrogen for 15 minutes, 1,1′-bis(diphenylphosphino)ferrocence palladium (II) chloride (0.060 g, 0.015 mmole) is added. The reaction is heated at 80° C. for 4 hours. The solvent is removed on rota-vapor, and the crude product is purified by column chromatography (silica gel, gradient elution 0-20% acetone in hexane) to provide a yellow oil (0.153 g, 65%). Mass [EI+] 409 (M+H)+, 817(M+H)+.

Workup

  1. customAfter bubbling with nitrogen for 15 minutes
  2. customThe solvent is removed on rota-vapor
  3. customthe crude product is purified by column chromatography (silica gel, gradient elution 0-20% acetone in hexane)

Sources & evidence

ORD record
ord-4457cf5e7fa04514b3ba8add40fd6165
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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