Diisopropylethylamine → 5-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amine

HRID 706448Notes

Reaction equation

HRID 706448 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.Cl[C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][C:25]([I:31])=[CH:24][N:23]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[I:31][C:25]1[CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[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)=[N:23][CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15142942-Chloro-5-iodo-3-nitropyridineHCID 118113971HCID 118113971, compound

Product 1

HCID 1181139925-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amineYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine (9.11 g, 33.21 mmol) in acetonitrile (150 mL) was added 2-chloro-5-iodo-3-nitropyridine (9.90 g, 34.81 mmol) and N,N-diisopropylethylamine (6.44 g, 49.81 mmol). The yellow solution was heated to reflux and stirred. After 3 h, the red-brown mixture was cooled to 0° C. resulting in the formation of a precipitate. The precipitate was isolated by filtration and washed with acetonitrile (50 mL) and water (200 mL). 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 14.67 g (85%) of 5-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amine as a yellow-brown solid.

Workup

  1. temperatureThe yellow solution was heated
  2. temperatureto reflux
  3. customresulting in the formation of a precipitate
  4. customThe precipitate was isolated by filtration
  5. washwashed with acetonitrile (50 mL) and water (200 mL)
  6. dissolutionThe moist solids were dissolved in dichloromethane
  7. customa small amount of water separated
  8. customwas removed
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-df8effb328b245989193de34f22c2bc8
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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