Cesium carbonate → HCID 86683845, compound

HRID 340434Notes

Reaction equation

HRID 340434 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O)=[O:13])([CH3:10])([CH3:9])[CH3:8].O1CCOCC1.[Br:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33](Br)[CH:34]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[C:7]([O:11][C:12]([N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:33]1[CH:32]=[N:31][CH:30]=[C:29]([Br:28])[CH:34]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 693693,5-DibromopyridineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 86683845HCID 86683845, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (165 mg), 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (136 mg) and Pd(PPh3)4 (24 mg) were added to a 1,4-dioxane (4 ml) solution containing 3,5-dibromopyridine (100 mg), followed by reflux for 4 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (silica gel: silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=4:1), and a white solid of tert-butyl2-(5-bromopyridin-3-yl)-1H-pyrrol-1-carboxylate (73 mg) was thus obtained.

Workup

  1. temperatureby reflux for 4 hours in a nitrogen atmosphere
  2. customThe organic layer was collected
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (silica gel: silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d4efe2fdfaf7477ab82ba0caa11d08f1
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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