Dichloromethane → HCID 58707324, compound

HRID 2426067Notes

Reaction equation

HRID 2426067 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:13])[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(C(C)C)CC)(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]([CH3:13])[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 58707318HCID 58707318, compound

Product 1

HCID 58707324HCID 58707324, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(5-Fluoro-2-methoxy-3-methylphenyl)ethanamine (0.34 g, 1.87 mmol), 2,4-difluoro-1-methanesulfonyl-benzene (0.3 g, 1.56 mmol) and 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 mL), 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-methylphenyl)ethyl)-2-(methylsulfonyl)benzenamine (83 mg, 14%): 1H NMR (400 MHz, CDCl3): δ 7.78 (dd, 1H), 7.07 (dd, 1H), 7.03 (dd, 1H), 6.53 (dd, 1H), 6.32 (dd, 1H), 4.82 (bs, 1H), 4.45 (m, 1H), 3.75 (s 3H), 3.07 (s, 3H), 2.41 (s, 3H), 1.48 (d, 3H).

Workup

  1. washwashed with water (2×20 mL), 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-9d7cac4ec23e403281f5d9e3fd13a815
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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