Pyridine → HCID 22482259, compound

HRID 2181819Notes

Reaction equation

HRID 2181819 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[CH:15]([NH2:17])[CH3:16].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.N1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[CH:15]([NH:17][S:26]([C:23]1[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=1)(=[O:28])=[O:27])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 224823471-(2',4-Difluoro-1,1'-biphenyl-2-yl)ethylamine

Product 1

HCID 22482259HCID 22482259, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 1-(2′,4-difluoro-1,1′-biphenyl-2-yl)ethylamine (0.26 g, 1.12 mmol) in dichloromethane (10 mL) was treated with 4-methoxybenzenesulfonyl chloride (0.23 g, 1.12 mmol), and pyridine (0.09 g, 1.12 mmol). The reaction was stirred at room temperature for twelve hours, diluted with dichloromethane, washed sequentially with a 1 N hydrochloric acid solution (2×) and a saturated, aqueous, sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered through a short column of silica gel, and evaporated to a residue which, after crystallization from ethyl acetate-hexane, afforded the title compound (0.22 g, 0.53 mmol, 48%) as a racemic, homogeneous, colorless, crystalline solid, m.p. 182-184° C.;

Workup

  1. washwashed sequentially with a 1 N hydrochloric acid solution (2×)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered through a short column of silica gel
  4. customevaporated to a residue which
  5. customafter crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4e8bf76f0218437d9be4d96f9de5bc90
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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