Cesium carbonate → HCID 86725407, compound

HRID 1503873Notes

Reaction equation

HRID 1503873 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[C:13]([CH3:15])[C:12](Br)=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[C:10]([F:17])=[CH:11][C:12]([N:28]2[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]2)=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 70556754HCID 70556754, compound

Product 1

HCID 86725407HCID 86725407, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A suspension of the product of Example 51A (3.2 g, 8.4 mmol), tert-butyl piperazine-1-carboxylate (1.9 g, 10.1 mmol), palladium(II) acetate (189 mg, 0.84 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.05 g, 1.7 mmol) and cesium carbonate (5.5 g, 16.8 mmol) in toluene (200 mL) was heated at reflux under nitrogen for 16 hours. After concentration, the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 10/1 petroleum ether/ethyl acetate to give the title compound. MS: 490 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 16 hours
  3. concentrationAfter concentration
  4. customthe residue was purified by flash chromatography on silica gel (200-300 mesh)
  5. washeluting with 10/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-01c16690387e4dc98f3cce8d70614203
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

Loading…