Dichloromethane → HCID 58707304, compound

HRID 1910619Notes

Reaction equation

HRID 1910619 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:10])[CH3:9])[CH:7]=1.F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[S:22]([CH3:25])(=[O:24])=[O:23].C(N(CC)C(C)C)(C)C.ClCCl>CN(C)C=O>[F:21][C:19]1[CH:20]=[CH:15][C:16]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:17]([NH:10][CH:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([Cl:13])[C:5]=2[O:11][CH3:12])[CH3:9])[CH:18]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 58707283HCID 58707283, compound

Product 1

HCID 58707304HCID 58707304, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(5-Fluoro-2-methoxy-3-chlorophenyl)ethanamine (0.38 g, 1.87 mmol), 2,4-difluoro-1-methanesulfonyl-benzene (0.3 g, 1.56 mmol) and N,N-diisopropylethylamine (1.4 mL, 7.81 mmol) in N,N-dimethylformamide (10 mL) was stirred at 110° C. for 18 h. Dichloromethane was added (20 mL) and washed with water (2×20), brine (20 mL), dried, and concentrated under reduced pressure to the crude compound which was purified by silica gel column (20% ethyl acetate in hexanes) to afford 5-fluoro-N-(1-(5-fluoro-2-methoxy-3-chlorophenyl)ethyl)-2-(methylsulfonyl)benzenamine (0.15 g, 26%): 1H NMR (400 MHz, CDCl3): δ 7.76 (dd, 1H), 7.06 (dd, 1H), 6.84 (dd, 1H), 6.79 (bs, 1H), 6.42 (dd, 1H), 6.19 (dd, 1H), 4.82 (m, 1H), 3.97 (s 3H), 3.05 (s, 3H), 1.58 (d, 3H).

Workup

  1. washwashed with water (2×20), brine (20 mL)
  2. customdried
  3. concentrationconcentrated under reduced pressure to the crude compound which
  4. customwas purified by silica gel column (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8bdc363ed8bc430aabea9c069a6a9469
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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