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Cesium fluoride → 1,1-Dimethylethyl 4-(4-fluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 900076
Notes
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Reaction equation

HRID 900076 reaction equation
FC(F)(F)C(O[C:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:11]=1)=O.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.[F-].[Cs+]>COCCOC.CO.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:21][C:22]1[CH:27]=[CH:26][C:25]([C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH:11]=2)=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 2856454-Fluorophenylboronic acidHCID 22179822tert-butyl 4-[(trifluoroacetyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 157514261,1-Dimethylethyl 4-(4-fluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylateYield 78.1%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 887MethanolSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of Example 6A (4.0 g, 12 mmol) and 4-fluorophenylboronic acid (1.68 g, 12 mmol) in 1,2-dimethoxyethane (100 mL) and methanol (50 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (0.416 g, 0.36 mmol) and CsF (3.64 g, 24 mmol), heated to reflux, and stirred overnight. The reaction was concentrated and the concentrate was dissolved in ethyl acetate (100 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:6 ethyl acetate/hexanes to provide the desired product (2.6 g, 78%). MS(CI) m/e 278 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated
  4. dissolutionthe concentrate was dissolved in ethyl acetate (100 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  6. washthe combined extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by flash column chromatography on silica gel with 1:6 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-972453154cce4bbe92a348c8bc169141
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07358251B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes