Cesium carbonate → N-(4-(4-Cyanophenyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392456Notes

Reaction equation

HRID 392456 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]Cl)[CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH2:28][C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 22663822N-(4-(4-Cyanophenyl)phenyl)-N-ethylsulfonylamine

Product 1

HCID 23521724N-(4-(4-Cyanophenyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-(4-cyanophenyl)phenyl)-N-ethylsulfonylamine (200 mg, 0.7 mmol), 3-picolyl chloride hydrochloride (123 mg, 0.75 mmol), and cesium carbonate (2.3 g, 7.0 mmol) was dissolved in 10 ml DMF and stirred for 18 h at room temperature. The mixture was diluted with 80 ml ethyl acetate, 20 ml water. The organic phase was separated and washed twice with 25 ml of water. The organic phase was then dried over sodium sulfate, filtered, and concentrated in vacuo to an oily residue. The residue was flushed through a 20 g mega bond elut silica column with 0 to 5% methanol/ethyl acetate. The desired fractions were concentrated in vacuo to afford the title compound. 1H NMR: 8.55 (bs,1H), 8.41 (bs,1H), 7.78 (d,1H,J=8 Hz), 7.72 (d,2H,J=12 Hz), 7.6 (d,2H,J=12 Hz), 7.52 (d,2H,J=12 Hz), 7.35 (d,2H,J=12 Hz), 7.29 (m,1H), 4.95 (s,1H), 3.15 (q,2H,J=8 Hz), 1.45 (t,3H,J=8 Hz). MS calcd. 377.5; MS (M+1) 378.2.

Workup

  1. customThe organic phase was separated
  2. washwashed twice with 25 ml of water
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to an oily residue
  6. customThe residue was flushed through a 20 g mega bond
  7. concentrationThe desired fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-bb030d11e0554e81980672268cb9d329
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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