Diisopropylethylamine → 4-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-2-nitroaniline

HRID 706424Notes

Reaction equation

HRID 706424 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][NH2:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1.F[C:22]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=1[N+:29]([O-:31])=[O:30].C(N(C(C)C)CC)(C)C>C(#N)C.O>[I:28][C:25]1[CH:26]=[CH:27][C:22]([NH:20][CH2:19][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]3[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[C:23]([N+:29]([O-:31])=[O:30])[CH:24]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 145905821-Fluoro-4-iodo-2-nitrobenzeneHCID 118113971HCID 118113971, compound

Product 1

HCID 1181140654-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-2-nitroanilineYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine (5.00 g, 18.23 mmol) in acetonitrile (75 mL) was added 1-fluoro-4-iodo-2-nitrobenzene (4.55 g, 17.04 mmol) and diisopropylethylamine (3.30 g, 25.56 mmol). The yellow solution was heated to reflux and stirred. After 4 h, the orange-brown mixture was allowed to cool to room temperature and was diluted with water (150 mL). The resulting bright orange precipitate was isolated by filtration and washed with water. The moist solids were dissolved in dichloromethane, and a small amount of water separated and was removed. The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 7.10 g (80%) of 4-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-2-nitroaniline as a bright orange solid.

Workup

  1. temperatureThe yellow solution was heated
  2. temperatureto reflux
  3. customThe resulting bright orange precipitate was isolated by filtration
  4. washwashed with water
  5. dissolutionThe moist solids were dissolved in dichloromethane
  6. customa small amount of water separated
  7. customwas removed
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d4079d971b614340983532b4ecdf127c
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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