Diisopropylethylamine → HCID 118114020, compound

HRID 706471Notes

Reaction equation

HRID 706471 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:20][NH2:21])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[CH3:2].Cl[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][C:26]([I:32])=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[CH2:20][NH:21][C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][C:26]([I:32])=[CH:25][N:24]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15142942-Chloro-5-iodo-3-nitropyridineHCID 118114093(3-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine

Product 1

HCID 118114020HCID 118114020, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine (2.75 g, 9.54 mmol) in acetonitrile (50 mL) was added 2-chloro-5-iodo-3-nitropyridine (2.85 g, 10.01 mmol) and N,N-diisopropylethylamine (1.85 g, 14.31 mmol). The resulting yellow mixture was heated to reflux. After 3 h, the red-brown solution was allowed to cool to room temperature, resulting in the formation of a precipitate. The solids were isolated by filtration and washed with water (200 mL). The moist solids were dissolved in dichloromethane (100 mL), and a small amount of water separated and was removed. The solution was dried over magnesium sulfate, filtered, and concentrated to provide 4.34 g (85%) of N-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-5-iodo-3-nitropyridin-2-amine as an orange solid.

Workup

  1. temperatureThe resulting yellow mixture was heated to reflux
  2. customresulting in the formation of a precipitate
  3. customThe solids were isolated by filtration
  4. washwashed with water (200 mL)
  5. dissolutionThe moist solids were dissolved in dichloromethane (100 mL)
  6. customa small amount of water separated
  7. customwas removed
  8. dry with materialThe solution was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-49ce3108efa748479a5b7c5e045f4a2f
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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