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Oxygen → 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-phenyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428719
Notes
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Reaction equation

HRID 1428719 reaction equation
Cl[C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:26])[CH:11]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[C:15]([F:25])[CH:14]=2)[CH3:12])=[CH:6][CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[N:3]=1.[C:31]1(C)[C:32](CCO)=[CH:33][CH:34]=[CH:35][CH:36]=1.C1(B(CO)CO)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].O=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:25][C:15]1[CH:14]=[C:13]([CH:11]([CH3:12])[C:10]([NH:9][CH2:8][C:7]2[C:2]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[N:3][C:4]([C:27]([F:30])([F:29])[F:28])=[CH:5][CH:6]=2)=[O:26])[CH:18]=[CH:17][C:16]=1[CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 977OxygenHCID 10340Sodium CarbonateHCID 882672-Methylphenethyl alcoholHCID 86679935N-((2-chloro-6-(trifluoromethyl)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)-phenyl)propanamideHCID 86680210(Phenylboranediyl)dimethanol

Product 1

HCID 71539475
2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-phenyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
Yield 84%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

The N-((2-chloro-6-(trifluoromethyl)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (100 mg, 0.214 mmol) was added to a mixture of 1.2 mL toluene-ethanol (8:2). After addition of (phenylboranediyl)dimethanol (39 mg, 0.324 mmol), 0.2 mL 2 M aqueous sodium carbonate solution and tetrakis(triphenylphosphine)palladium (0) (25 mg) the mixture was heated at 100° C. for 1 h in a microwave. The reaction mixture was free from oxygen by evacuating and flushing with nitrogen. After cooling to room temperature the reaction mixture was diluted with 15 mL water, extracted with ethyl acetate (2×15 mL), dried over magnesium sulfate and concentrated under reduced pressure. The solid obtained was purified by column chromatography (silica gel: 100-200 mesh, eluent: cyclohexane/ethyl acetate 2:3) to afford 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-phenyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 5) (92 mg, 84%).

Workup

  1. customby evacuating
  2. customflushing with nitrogen
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. additionwas diluted with 15 mL water
  5. extractionextracted with ethyl acetate (2×15 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe solid obtained
  9. customwas purified by column chromatography (silica gel: 100-200 mesh, eluent: cyclohexane/ethyl acetate 2:3)

Sources & evidence

ORD record
ord-176e2352d2c847daa9d44b90c065924e
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937092B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes