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1,2-Dimethoxyethane → 4-(5-Fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

HRID 32263
Notes
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Reaction equation

HRID 32263 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH:24]=[C:23](OS(C(F)(F)F)(=O)=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].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.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH:22]=[C:23]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:11][CH3:12])[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 597694194-(5-Fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl esterYield 127.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 5-fluoro-2-methoxyphenylboronic acid (1 g, 5.88 mmol), 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.22 g, 7.64 mmol) (David J. Wustrow, Lawrence D. Wise, Synthesis, 1991, 993) and 1,2-dimethoxyethane (30 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.29 mmol) and 2N aqueous solution of sodium carbonate (8.82 mL, 17.6 mmol), followed by stirring for 2 hours at an external temperature of 90° C. under a nitrogen atmosphere. Brine was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the filtrate was concentrated to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 2.3 g of the title compound as a yellow oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. concentrationthe filtrate was concentrated
  3. customto give a residue, which
  4. customwas purified by silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-2ce25b6d60274551be58ef7c1660ab8c
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425554B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes