Cesium carbonate → HCID 23521706, compound

HRID 392460Notes

Reaction equation

HRID 392460 reaction equation
[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:5])=[O:4])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br>CN(C)C=O.C(OCC)(=O)C>[I:20][C:21]1[CH:22]=[C:23]([CH2:24][N:6]([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27593613-Iodobenzyl bromideHCID 4135863HCID 4135863, compound

Product 1

HCID 23521706HCID 23521706, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(ethylsulfonyl)pyrid-3-ylmethylamine (1.1 g, 5.5 mmol), cesium carbonate (1.79 g, 5.5 mmol), and 3-iodobenzyl bromide (1.64 g, 5.5 mmol) was stirred in N,N-dimethylformamide (25 ml) for 5 h at room temperature. The mixture was diluted with ethyl acetate (100 ml) and washed four times with water (50 ml). The organics were separated, dried over sodium sulfate, filtered, and concentrated in vacuo to a crude residue. The residue was purified by radial chromatography on a 4 micron silica plate eluting with 3% methanol/dichloromethane to afford the title compound. 1H NMR: 8.6 (d,1H,J=4 Hz), 8.41 (s,1H), 7.75 (m,1H), 7.65 (m,1H), 7.60 (s,1H), 7.25-7.40 (m,2H), 7.08 (m,1H), 4.43 (s,2H), 4.33 (s,2H), 3.08 (q,2H,J=8 Hz), 1.43 (t,3H,J=8 Hz). MS calcd. 416.3; MS (M+1) 417.1.

Workup

  1. washwashed four times with water (50 ml)
  2. customThe organics were separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a crude residue
  6. customThe residue was purified by radial chromatography on a 4 micron silica plate
  7. washeluting with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-68bb8308d31d4294a3f2c2bd97400624
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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