Sodium Carbonate → HCID 19705303, compound

HRID 1809788Notes

Reaction equation

HRID 1809788 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:33]2[CH:32]=[C:31]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:36]=[CH:35][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734315(3-Phenylphenyl)boronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 19705303HCID 19705303, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.98 g, 12 mmol), 3-biphenylboronic acid (2.77 g, 14 mmol), LiCl (1.53 g, 36 mmol), dimethoxyethane (35 mL), tetrakis-(triphenylphosphin)-palladium (0.81 g, 0.7 mmol) and Na2CO3 (2M solution, 14 mL, 28 mmol) is heated at reflux under argon for 14 h. The mixture is cooled to RT, dimethoxyethane is removed in vacuo and the residue is diluted with aqueous 2N Na2CO3 solution containing a few mL of concentrated NH4OH. The aqueous layer is extracted three times with CH2Cl2. The combined organic extracts are dried (Na2SO4) and evaporated in vacuo. Flash chromatography of the dark residue (SiO2, hexane/ethyl acetate) affords 4-biphenyl-3-yl-3,6,dihydro-2H-pyridine-1-carboxylic acid t-butyl ester as a colourless oil: MS (after treatment with trifluoroacetic acid) 236.3 [M+H—C5H8O2]+; Rf 0.40 (hexane/ethyl acetate 8:2).

Workup

  1. temperatureis heated
  2. temperatureat reflux under argon for 14 h
  3. customdimethoxyethane is removed in vacuo
  4. additionthe residue is diluted with aqueous 2N Na2CO3 solution
  5. additioncontaining a few mL of concentrated NH4OH
  6. extractionThe aqueous layer is extracted three times with CH2Cl2
  7. dry with materialThe combined organic extracts are dried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a051eb8a3e6842cf9cfcdae8ed60c192
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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