Sodium Carbonate → tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2223702Notes

Reaction equation

HRID 2223702 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.[Cl-].[Li+].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH:31]=[C:30](S(C(F)(F)F)(=O)=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>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.CCOC(C)=O.C(Cl)Cl.COCCOC>[C:20]([O:24][C:25]([N:27]1[CH2:28][CH:29]=[C:30]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])[CH2:31][CH2:32]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27339582-Methoxyphenylboronic acidHCID 21193094Tert-butyl 4-((trifluoromethyl)sulfonyl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 22629561tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A three necked flask purged with nitrogen is charged with aqueous 2N Na2CO3 (1.4 mL), 1,2-dimethoxyethane (3.7 mL), 2-methoxyphenyl boronic acid (206 mg, 1.35 mmol), anhydrous lithium chloride (123 mg, 2.9 mmol), 4-trifluoromethanesulfonyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (321 mg, 0.96 mmol) and tetrakis(triphenylphosphine)palladium (56 mg, 0.048 mmol). The mixture is stirred at reflux for 2 h under nitrogen, cooled and concentrated under reduced pressure. The residue is partitioned between CH2Cl2 (10 mL), aqueous 2N Na2CO3 (10 mL), and concentrated NH4OH (1 mL). The aqueous layer is extracted twice with CH2Cl2. The combined organic layers are dried (MgSO4), filtered and concentrated to provide a crude oil. Flash chromatography (Hex/AcOEt/CH2Cl2: 5/1/1) provides the title compound.

Workup

  1. customA three necked flask purged with nitrogen
  2. temperatureat reflux for 2 h under nitrogen
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is partitioned between CH2Cl2 (10 mL), aqueous 2N Na2CO3 (10 mL), and concentrated NH4OH (1 mL)
  6. extractionThe aqueous layer is extracted twice with CH2Cl2
  7. dry with materialThe combined organic layers are dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide a crude oil

Sources & evidence

ORD record
ord-be28a7eec9aa401babc598277d43fdfc
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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