Cesium carbonate → HCID 58503974, compound

HRID 2407801Notes

Reaction equation

HRID 2407801 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:14])[CH:3]=1.Br[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[N:29][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N:29]1[CH:30]=[C:25]([CH2:24][N:20]2[CH2:21][CH2:22][CH:17]([CH2:16][NH:15][C:13](=[O:14])[C:4]3[CH:3]=[C:2]([NH2:1])[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=3)[CH2:18][CH2:19]2)[CH:26]=[CH:27][C:28]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 103322782,2'-Bipyridine, 5-(bromomethyl)-HCID 58503970HCID 58503970, compound

Product 1

HCID 58503974HCID 58503974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound prepared in Example 334 (0.009 g), 5-(bromomethyl)-2,2′-bipyrdine (0.008 g, prepared according to the reported preparation in Journal of the American Chemical Society, 2006, 128(1), 250-256) and cesium carbonate (0.019 g) were heated to 80° C. for 16 hours in N,N-dimethylformamide (2 mL). The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 1-4% (9:1 methanol:ammonium hydroxide)/ethyl acetate) to furnish the title compound (0.006 g) having the following physical data.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  2. washThe organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant: 1-4% (9:1 methanol:ammonium hydroxide)/ethyl acetate)

Sources & evidence

ORD record
ord-b9bcb8ef479141f3aba87e34c53ab053
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…