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Potassium Iodide → methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HRID 1187228
Notes
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Reaction equation

HRID 1187228 reaction equation
[I-].[K+].Br[CH:4]([C:6]1[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[CH:12][C:11]2=[O:22])[CH3:5].[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([F:36])[CH:35]=1)[NH:31][CH3:32]>C(Cl)(Cl)Cl.CO>[F:27][C:28]1[CH:29]=[C:30]([N:31]([CH3:32])[CH:4]([C:6]2[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=[C:10]3[C:15]=2[O:14][C:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:12][C:11]3=[O:22])[CH3:5])[CH:33]=[C:34]([F:36])[CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 167203773,5-difluoro-N-methylanilineHCID 58234984methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 58235022methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylateYield 81.2%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6212ChloroformSolvent

Procedure

Potassium iodide (1.521 g, 9.16 mmol) was added to a suspension of methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (3.3 g, 8.33 mmol, as described in Example 2.00) and 3,5-difluoro-N-methylaniline (3.58 g, 24.99 mmol) in CHCl3 (16 mL) and MeOH (4 mL). The mixture was stirred at RT over the weekend. The reaction mixture was concentrated to dryness and the resulting dark oil was triturated with diethyl ether to give a solid which was collected by filtration. This solid was suspended in water and pH was adjusted to 6-7 with 2N NaOH. The crude product was filtered and washed with ether, dried and purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM. The solvent was evaporated to dryness to afford methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (3.1 g, 81%) as a white solid. Mass Spectrum: M+H+ 459.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe resulting dark oil was triturated with diethyl ether
  3. customto give a solid which
  4. filtrationwas collected by filtration
  5. filtrationThe crude product was filtered
  6. washwashed with ether
  7. customdried
  8. custompurified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM
  9. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-4a9598f9683a43fba6c949f98eba6074
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673906B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes