Cesium carbonate → HCID 58042798, compound

HRID 564172Notes

Reaction equation

HRID 564172 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:22][C:23]([F:41])([F:40])[C:24]([N:26]1[CH2:32][CH2:31][C:30]2[CH:33]=[CH:34][C:35]([CH2:37][CH2:38]I)=[CH:36][C:29]=2[CH2:28][CH2:27]1)=[O:25]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:38][CH2:37][C:35]2[CH:34]=[CH:33][C:30]3[CH2:31][CH2:32][N:26]([C:24](=[O:25])[C:23]([F:22])([F:41])[F:40])[CH2:27][CH2:28][C:29]=3[CH:36]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 59822101HCID 59822101, compound

Product 1

HCID 58042798HCID 58042798, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 152 mg (0.76 mmol) 4-benzyloxy-1H-pyridin-2-one in THF at 0° C. is added subsequently 492 mg (1.51 mmol) cesium carbonate, 14 mg (0.08 mmol) tetra-butylammonium-iodide and 300 mg (0.76 mmol) 2,2,2-trifluoro-1-[7-(2-iodo-ethyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-ethanone (preparation 6b). The reaction mixture is stirred overnight at RT, diluted with DMF and filtered. The residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 5:95).

Workup

  1. filtrationfiltered
  2. customThe residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 5:95)

Sources & evidence

ORD record
ord-ae656b49aa6d414ebb47e95a15a56193
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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