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Aniline → (2Z)-3-anilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-3-(isopropylamino)-2-propen-1-one

HRID 2183777
Notes
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Reaction equation

HRID 2183777 reaction equation
Cl[C:2](Cl)=[CH:3][C:4]([C:6]1[C:7]([Cl:14])=[N:8][C:9]([Cl:13])=[C:10]([F:12])[CH:11]=1)=[O:5].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH:23]([NH2:26])([CH3:25])[CH3:24]>C(Cl)Cl.O1CCOCC1>[NH:16](/[C:2](/[NH:26][CH:23]([CH3:25])[CH3:24])=[CH:3]\[C:4]([C:6]1[C:7]([Cl:14])=[N:8][C:9]([Cl:13])=[C:10]([F:12])[CH:11]=1)=[O:5])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6115AnilineHCID 6363IsopropylamineHCID 219481323,3-Dichloro-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one

Product 1

HCID 60061202(2Z)-3-anilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-3-(isopropylamino)-2-propen-1-oneYield 10%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

3,3-dichloro-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one (374.0 mg, 1.29 mmol) was dissolved in CH2Cl2 (5 mL) and cooled to 10° C. Aniline (120.0 mg, 1.29 mmol) and isopropylamine (76.5 mg, 1.29 mmol) were added dropwise as a mixture in 3 mL of 1,4-dioxane. TEA (0.897 mL, 6.45 mmol) was added and the reaction mixture was warmed to room temperature and left to stir for 2 h. The dioxane was removed in vacuo and the brown residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue using Biotage silica gel chromatography eluting with 6:1 to 7:3 Hex:EtOAc provided (2Z)-3-anilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-3-(isopropylamino)-2-propen-1-one (45 mg, 10%) as an off-white solid: LCMS RT: 3.63 min, MH+: 3-68.2.

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. waitleft
  3. customThe dioxane was removed in vacuo
  4. customthe brown residue was partitioned between EtOAc and saturated aqueous NaHCO3
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue
  10. washeluting with 6:1 to 7:3 Hex

Sources & evidence

ORD record
ord-482fd62b3dfb4b8eb9fd1396efe56f36
Source dataset
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06900205B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes