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Water → ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate

HRID 1183984
Notes
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Reaction equation

HRID 1183984 reaction equation
O.C(=O)([O-])[O-].[K+].[K+].[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[C:18]1[CH:23]=[CH:22][N:21]([CH2:24][CH2:25][C:26]([CH3:36])([S:32]([CH3:35])(=[O:34])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:20](=[O:37])[C:19]=1[CH3:38]>O1CCOCC1.[Pd]>[CH3:36][C:26]([S:32]([CH3:35])(=[O:34])=[O:33])([CH2:25][CH2:24][N:21]1[CH:22]=[CH:23][C:18]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:19]([CH3:38])[C:20]1=[O:37])[C:27]([O:29][CH2:30][CH3:31])=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 67249750ethyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 67248376ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Water (1 mL) was added to a suspension of potassium carbonate (392 mg, 2.84 mg), phenylboronic acid (76.1 mg, 0.624 mmol), and ethyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate (250 mg, 0.567 mmol) in 1,4-dioxane (5 mL) at ambient temperature. To this mixture was added Pd EnCat™ (154 mg, 0.06 mmol) and the mixture was stirred at 80° C. overnight. The mixture was cooled to ambient temperature, filtered, diluted with ethyl acetate and washed with water. To the organic extract was added silica gel and the mixture was concentrated to dryness. The material was purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate as an oil. 118.3 mg

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. extractionTo the organic extract
  6. additionwas added silica gel
  7. concentrationthe mixture was concentrated to dryness
  8. customThe material was purified via silica gel chromatography
  9. washeluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-32e33d2981194b5dbab50d39adcc9353
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664401B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes