Cesium carbonate → HCID 68568772, compound

HRID 1865432Notes

Reaction equation

HRID 1865432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][N:12]=[C:11]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[N:17]4)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:31]([C:33]1[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:35][CH:34]=1)[CH3:32]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[N:17]4)[N:12]([CH:31]([C:33]3[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])=[CH:35][CH:34]=3)[CH3:32])[N:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67484052HCID 67484052, compoundHCID 178478178HCID 178478178, compound

Product 1

HCID 68568772HCID 68568772, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the intermediate from step E (330 mg, 0.97 mmol) in 8 mL of anhydrous DMF was added Cs2CO3 (473 mg, 1.45 mmol) followed by tert-butyl 4-(1-bromoethyl)benzoate (331 mg, 1.16 mmol). The reaction was stirred at room temperature overnight and then diluted with water. The aqueous layer was then extracted with EtOAc (3×) and the combined organic layers were then washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting oil was purified by flash chromatography (20% EtOAc/Hexanes) to give the product as a yellow oil. 1H NMR (CDCl3, 500 MHz): 1.60 (s, 9H), 2.02 (d, J=7.1 Hz, 3H), 5.67 (q, J=7.1 Hz, 1H), 6.78 (s, 1H), 7.26 (d, J=8.2 Hz, 2H), 7.34 (t, J=1.8 Hz, 1H), 7.68 (dd, J=8.7, 1.9 Hz, 1H), 7.83 (d, J=1.8, 2H), 7.95 (d, J=8.2 Hz, 2H), 8.10 (d, J=1.9, 1H), 8.18 (d, J=8.7, 1H), 8.94 (s, 2H). LC-MS: 4.74, 4.89 min. (M+H)=546.46.

Workup

  1. extractionThe aqueous layer was then extracted with EtOAc (3×)
  2. washthe combined organic layers were then washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by flash chromatography (20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c059ed7b1ec34724b5647b2d7254f17c
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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