Sodium hydride → HCID 86702336, compound

HRID 2279081Notes

Reaction equation

HRID 2279081 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH2:12])[C:7]([O:10][CH3:11])=[N:8][CH:9]=1.[Cl:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[C:16](Cl)[N:15]=1>O1CCCC1>[Cl:13][C:14]1[N:15]=[C:16]([NH:12][C:6]2[C:7]([O:10][CH3:11])=[N:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)[C:17]([N+:21]([O-:23])=[O:22])=[CH:18][C:19]=1[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 122654282,6-Dichloro-3-methyl-5-nitropyridineHCID 451221815-Chloro-2-methoxypyridin-3-amine

Product 1

HCID 86702336HCID 86702336, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.23 g, 5.80 mmol) was added to a stirred solution of 5-chloro-2-methoxypyridin-3-amine (Preparation 23b, 1.15 g, 7.25 mmol) in tetrahydrofuran (11 mL) and the resulting mixture was stirred at ambient temperature for 30 minutes. A solution of 2,6-dichloro-3-methyl-5-nitropyridine (prepared according to the method described in WO2010/094645(A1), 1.0 g, 4.83 mmol) in tetrahydrofuran (10 mL) was then added and the reaction mixture was heated at reflux overnight and then stirred at ambient temperature for 3 days. Solvent was evaporated under reduced pressure and the resulting residue was treated with methanol, filtered, washed with additional methanol and dried to yield the title compound (1.18 g, 74%) as an orange solid.

Workup

  1. additionwas then added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux overnight
  4. stirringstirred at ambient temperature for 3 days
  5. customSolvent was evaporated under reduced pressure
  6. additionthe resulting residue was treated with methanol
  7. filtrationfiltered
  8. washwashed with additional methanol
  9. customdried

Sources & evidence

ORD record
ord-285bea241078488c8204b0a7d76486f2
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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