HCID 46449, compound → HCID 58707347, compound

HRID 1910600Notes

Reaction equation

HRID 1910600 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[NH2:15].F[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[S:24]([CH3:27])(=[O:26])=[O:25].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[F:23][C:21]1[CH:22]=[CH:17][C:18]([S:24]([CH3:27])(=[O:26])=[O:25])=[C:19]([NH:15][CH:8]2[C:9]3[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=3[O:13][CH3:14])[CH2:5][CH2:6][CH2:7]2)[CH:20]=1

Participants

6

Reactant 3

HCID 46449HCID 46449, compoundHCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzene

Product 1

HCID 58707347HCID 58707347, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-5,8-dimethoxynaphthalen-1-amine (1.1 g mL, 5.31 mmol), 2,4-difluoro-1-(methylsulfonyl)benzene (1.02 g, 5.31 mmol) and diisopropylethylamine (3.7 mL, 21.26 mmol) in N,N-dimethylformamide (10 mL) was stirred at 90° C. for 16 h. The reaction mixture was diluted with water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried, and concentrated under reduced pressure to yield 1.95 g of a yellow oil. The residue was purified by PTLC (25% ethyl acetate in hexanes) to give 1.26 g (63%) of the desired aniline: 1H NMR (400 MHz, CDCl3) δ 7.40 (dd, 1H), 6.73 (d, 1H), 6.66 (m, 2H), 6.44 (dt, 1H), 6.22 (br d, 1H), 4.79 (br s, 1H), 3.80 (s, 3H), 3.67 (s, 3H), 2.96-2.88 (m, 4H), 2.46-2.37 (m, 1H), 2.17-2.12 (br d, 1H), 1.92-1.84 (m, 1H), 1.78-1.60 (m, 2H). MS (ESI) m/z: Calculated: 379.13; Observed: 402.2 (M++23).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f3b6fd8f1b94d09a6dc5559e4e3cec2
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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