Ethanol → HCID 11483333, compound

HRID 1350895Notes

Reaction equation

HRID 1350895 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[O:14][C:15](Br)=[CH:16][CH:17]=1)=[O:12])[CH2:3]2.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)C>COCCOC.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.O>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[O:14][C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][CH:17]=1)=[O:12])[CH2:3]2

Participants

8

Reactant 4

HCID 702EthanolHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 68962369HCID 68962369, compound

Product 1

HCID 11483333HCID 11483333, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

(R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)(5-bromofuran-2-carboxamide) hydrochloride (100 mg), phenylboronic acid (45 mg), tetrakis(triphenylphosphine)palladium(0) (20 mg), cesium carbonate (547 mg), in a mixture of 1,2-dimethoxyethane (6 mL), ethanol (1.5 mL) and water (1 mL) were stirred under reflux under a nitrogen atmosphere for 17 h. The solution was evaporated and the residue was dissolved in chloroform. The solution was washed with aqueous sodium carbonate and the organic layer was then dried (Mg2SO4), filtered, and evaporated. HPLC purification using a gradient of 1:1 ammoniated methanol in chloroform, and chloroform gave the title compound as a colourless solid (63 mg); MS (ES+) 297 (MH+).

Workup

  1. temperatureunder reflux under a nitrogen atmosphere for 17 h
  2. customThe solution was evaporated
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe solution was washed with aqueous sodium carbonate
  5. dry with materialthe organic layer was then dried (Mg2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customHPLC purification

Sources & evidence

ORD record
ord-bcda2f14fde54a5da96c9f40a9b50431
Source dataset
uspto-grants-2007_05
Patent number
US07214688B2

Reaction notes

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