Diisopropylethylamine → N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine

HRID 1910577Notes

Reaction equation

HRID 1910577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:10])[CH3:9])[CH:7]=1.F[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[S:23]([CH3:26])(=[O:25])=[O:24].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH:10][C:18]2[CH:19]=[C:20]([F:22])[CH:21]=[CH:16][C:17]=2[S:23]([CH3:26])(=[O:25])=[O:24])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 509992651-(5-Chloro-2,3-dimethoxyphenyl)ethylamine

Product 1

HCID 44240863N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamineYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl amine (1.27 g, 5.89 mmol), 2,4-difluoro-1-methanesulfonyl-benzene (1.25 g, 6.48 mmol) and N,N-diisopropylethylamine (2.1 mL, 11.78 mmol) in acetonitrile was stirred at 80° C. for 48 h. The solvent was concentrated in vacuo, the residue was taken up in dichloromethane and washed with water, dried, and concentrated under reduced pressure to the crude compound which was purified by silica gel column (20% ethyl acetate in hexanes) to afford [1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl]-(5-fluoro-2-methanesulfonyl-phenyl)-amine (700 mg, 32%): 1H NMR (400 MHz, CDCl3): δ 7.74 (dd, 1 H), 6.82 (m, 2 H), 6.73 (dd, 1 H), 6.42 (dd, 1 H), 6.24 (dd, 1 H), 4.82 (m, 1 H), 3.95 (s 3 H), 3.88 (s,3 H), 3.27 (3, 3 H), 1.58 (s, 3 H).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure to the crude compound which
  5. customwas purified by silica gel column (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-33a15412e01042978188ee41ede5bcc4
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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