Potassium Carbonate → HCID 86715489, compound

HRID 2284580Notes

Reaction equation

HRID 2284580 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16](F)[CH:15]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][NH2:33])[CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([NH:33][CH2:32][CH2:31][N:28]4[CH2:29][CH2:30][O:25][CH2:26][CH2:27]4)[CH:15]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4082852-MorpholinoethylamineHCID 86715490HCID 86715490, compound

Product 1

HCID 86715489HCID 86715489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To solution of 2-(4-fluoro-3-methylphenyl)-3-(3-fluoro-4-nitrophenyl)pyridine (100 mg) in 2 ml, THF was added 2-morpholinoethanamine (64 uL) and K2CO3 (76 mg). The reaction was heated at 60° C. for 15 hours in a sealed vial. The reaction mixture was cooled to room temperature, concentrated by rotary evaporation under vacuum and partitioned the concentrate between CH2Cl2/water. The organic layer was separated, dried with anhydrous Na2SO4, filtered and evaporated. The crude residue of 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-N-(2-morpholinoethyl)-2-nitrobenzenamine was used in the next step with no further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated by rotary evaporation under vacuum
  3. custompartitioned the
  4. concentrationconcentrate between CH2Cl2/water
  5. customThe organic layer was separated
  6. dry with materialdried with anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue of 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-N-(2-morpholinoethyl)-2-nitrobenzenamine was used in the next step with no further purification

Sources & evidence

ORD record
ord-74f73ae872e04845b0d27a2984909e76
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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