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Water → Methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylate

HRID 1091743
Notes
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Reaction equation

HRID 1091743 reaction equation
IC.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[C:14]([C:20]([O:22][CH3:23])=[O:21])=[C:15]([CH3:19])[NH:16][C:17]=2[CH3:18])=[O:12])=[CH:6][C:5]=1[C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28][CH2:27]1)=[O:25].[C:34](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[C:14]([C:20]([O:22][CH3:23])=[O:21])=[C:15]([CH3:19])[N:16]([CH3:34])[C:17]=2[CH3:18])=[O:12])=[CH:6][C:5]=1[C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28][CH2:27]1)=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 57791818methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 57791825Methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylate
Yield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.029 mL, 0.46 mmol) was added to methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (57) (0.100 g, 0.23 mmol) and potassium carbonate (0.048 g, 0.35 mmol) in DMF (5 mL). The resulting suspension was stirred at room temperature for 16 hours. The reaction was incomplete and further iodomethane (0.029 mL, 0.46 mmol) was added and the suspension was stirred at room temperature for a further 4 hours. The reaction was incomplete so the temperature was increased to 50° C. and the reaction mixture was stirred for a further 3 hours. The reaction mixture was poured into water (75 mL), extracted with EtOAc (3×50 mL), the combined organic layers were washed with water (50 mL) and saturated brine (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a colourless gum (0.082 g, 79% yield); m/z (LC-MS, ESI+), RT=2.06 min (M+H=445.30).

Workup

  1. stirringthe suspension was stirred at room temperature for a further 4 hours
  2. temperaturewas increased to 50° C.
  3. stirringthe reaction mixture was stirred for a further 3 hours
  4. extractionextracted with EtOAc (3×50 mL)
  5. washthe combined organic layers were washed with water (50 mL) and saturated brine (50 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford crude product
  10. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane
  11. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-eb2840e287664ddbb56d98efc178fe70
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129380B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes