Cesium fluoride → HCID 22479243, compound

HRID 2182590Notes

Reaction equation

HRID 2182590 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[CH2:11][CH2:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1.[F-].[Cs+]>COCCOC>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:2]2[CH:27]=[CH:26][C:5]([CH2:6][C:7]34[C:15](=[O:16])[N:14]([C:17]5[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=5)[C:13](=[O:25])[N:12]3[CH2:11][CH2:10][CH2:9][CH2:8]4)=[CH:4][CH:3]=2)[CH:29]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 27343783-Pyridinylboronic acidHCID 22479114HCID 22479114, compound

Product 1

HCID 22479243HCID 22479243, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,8-diazabicyclo(4.3.0]nonane-7,9-dione (0.360 g) and 3-pyridineboronic acid (0.225 g) in DME (20 mL) was added CsF (0.615 g) and the mixture was degassed with nitrogen. After 10 minutes, Pd(PPh3)4 was added and the mixture was heated under reflux for 6 hours. The reaction mixture was concentrated. The residue was redissolved in EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (Silica gel: hexane/acetone: 3/2, Chromatotron) afforded the titled compound (0.172 g). MS (m/z) 466 (MH+). mp 276.5° C.

Workup

  1. customthe mixture was degassed with nitrogen
  2. additionPd(PPh3)4 was added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 6 hours
  5. concentrationThe reaction mixture was concentrated
  6. dissolutionThe residue was redissolved in EtOAc
  7. washwashed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by chromatography (Silica gel: hexane/acetone: 3/2, Chromatotron)

Sources & evidence

ORD record
ord-0dc9d26255af4f37ac2c473a8f0c95dc
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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