Pyridine → HCID 23521726, compound

HRID 392426Notes

Reaction equation

HRID 392426 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:28][C:29]([F:36])([F:35])[CH2:30][S:31](Cl)(=[O:33])=[O:32].C([O-])([O-])=O.[K+].[K+]>ClC(Cl)C>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:31]([CH2:30][C:29]([F:36])([F:35])[F:28])(=[O:33])=[O:32])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 69880691N-[4-(Phenylmethyl)phenyl]-3-pyridinemethanamine

Product 1

HCID 23521726HCID 23521726, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of N-(4-benzylphenyl)pyrid-3-ylmethylamine (0.517 g, 1.88 mmol) dissolved in 8 mL dichloroethane and 4 mL pyridine at 0° C. was added 2,2,2-trifluoroethylsulfonyl chloride (0.313 mL, 2.83 mmol). The reaction was stirred at ambient temperature overnight. The mixture was treated with 1.5 g anhydrous K2CO3 and stirred for 2 h. Then the mixture was filtered and concentrated. The residue was chromatographed on silica gel with 3:1 to 2:1 DCM/EtOAc to give an amorphous white solid. 1H NMR: 8.52 (br d,J=3.3 Hz, 1H), 8.32 (br s,1H), 7.71 (dt,J=6.8, 1.4 Hz, 1H), 7.33-7.20 (m,4H), 7.18-7.10 (m,6H), 4.88 (s,2H), 3.95 (s,2H), 3.79 (q,J=9.3 Hz, 2H).

Workup

  1. stirringstirred for 2 h
  2. filtrationThen the mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel with 3:1 to 2:1 DCM/EtOAc
  5. customto give an amorphous white solid

Sources & evidence

ORD record
ord-902e863b65c84b298b8e11e450cf0b63
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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