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Triethylamine → n-Butyl 3-(2-(methylamino)-5-nitropyridin-3-yl)acrylate

HRID 1620076
Notes
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Reaction equation

HRID 1620076 reaction equation
C(N(CC)CC)C.[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:11])[CH:9]=[CH2:10].C1(C)C(C(P(C(C2C(C)=CC=CC=2)=O)C(C2C(C)=CC=CC=2)=O)=O)=CC=CC=1.Br[C:46]1[C:47]([NH:55][CH3:56])=[N:48][CH:49]=[C:50]([N+:52]([O-:54])=[O:53])[CH:51]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[CH3:56][NH:55][C:47]1[C:46]([CH:10]=[CH:9][C:8]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])=[CH:51][C:50]([N+:52]([O-:54])=[O:53])=[CH:49][N:48]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8846Butyl Acrylate2×HCID 164772163-bromo-N-methyl-5-nitropyridin-2-amineHCID 19696886Tri(o-toluoyl)phosphine2×

Product 1

HCID 77522859n-Butyl 3-(2-(methylamino)-5-nitropyridin-3-yl)acrylate

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
2×
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (32 μl), n-butyl acrylate (33 μl), tri(o-toluoyl)phosphine (24 mg), and palladium acetate (5 mg) were added to a tube containing a DMF (3 ml) solution containing 3-bromo-N-methyl-5-nitropyridin-2-amine (45 mg) and the tube was sealed, followed by stirring at 100° C. for 8 hours. The reaction solution was adjusted to room temperature, and n-butyl acrylate (33 μl), tri(o-toluoyl)phosphine (24 mg), and palladium acetate (5 mg) were added again to the tube and the tube was sealed, followed by stirring at 100° C. for 9 hours. Further, the reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=16:1 to 3:1), and a yellow solid of n-butyl 3-(2-(methylamino)-5-nitropyridin-3-yl)acrylate (44 mg) was thus obtained.

Workup

  1. customthe tube was sealed
  2. customwas adjusted to room temperature
  3. customthe tube was sealed
  4. stirringby stirring at 100° C. for 9 hours
  5. customwas adjusted to room temperature
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe resultant was washed with saturated saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationSubsequently, the solvent was distilled away under reduced pressure
  10. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=16:1 to 3:1)

Sources & evidence

ORD record
ord-47a7d04e985f4e87987a25cebfc18664
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772320B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes