Cesium carbonate → HCID 66691115, compound

HRID 1469196Notes

Reaction equation

HRID 1469196 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[S:32][C:33]([Cl:38])=[C:34]([CH2:36]Br)[CH:35]=2)[O:11][C@@H:10]1[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:48][C:49]1[CH:54]=[CH:53][C:52](B(O)O)=[CH:51][CH:50]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCO>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[S:32][C:33]([Cl:38])=[C:34]([CH2:36][C:52]3[CH:53]=[CH:54][C:49]([CH3:48])=[CH:50][CH:51]=3)[CH:35]=2)[O:11][C@@H:10]1[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 66693973HCID 66693973, compound

Product 1

HCID 66691115HCID 66691115, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of bromide 38 (850 mg, 1.16 mmol) in toluene/EtOH (18 mL/2 mL) were added 4-methylphenylboronic acid (200 mg, 1.39 mmol), tetrakis(triphenylphosphin)palladium (70 mg, 0.058 mmol) and Cs2CO3 (770 mg, 2.32 mmol) at room temperature. The mixture was stirred at 120° C. The mixture was cooled to room temperature and filtered off thorough silica gel to remove insoluble materials. The filtrate was ure was extracted with EtOAc/H2O (100 mL/150 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the title compound 39 (611 mg, 71%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered off thorough silica gel
  3. customto remove insoluble materials
  4. extractionwas extracted with EtOAc/H2O (100 mL/150 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-3b0e731bb3264534a10f559469464f2c
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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