Acetonitrile → 3-[3-(2-Methyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

HRID 498237Notes

Reaction equation

HRID 498237 reaction equation
CO[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[CH:11]=2)[CH:5]=1.[C:18]([C:21]1C=C(B(O)O)C=CC=1)([OH:20])=[O:19].Br[C:31]1[CH:36]=[CH:35]N=C(C)C=1.O=S(Cl)Cl.[C:42](#N)C>C([O-])([O-])=O.[Na+].[Na+].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:36]([O:20][C:18](=[O:19])[CH2:21][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[CH:11]=2)[CH:5]=1)=[O:17])([CH3:35])([CH3:31])[CH3:42]

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 24386Thionyl ChlorideHCID 27339573-Carboxyphenylboronic acidHCID 27628354-Bromo-2-methylpyridineHCID 694891453-(2-Methyl-pyridin-4-yl)-benzoic acid methyl ester

Product 1

HCID 694893073-[3-(2-Methyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

The title compound was prepared from 3-(2-methyl-pyridin-4-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of 3-carboxyphenylboronic acid (7.13 g, 43.0 mmol) and 4-bromo-2-methylpyridine [Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] (7.40 g, 43.0 mmol) in acetonitrile (215 ml) and 0.4M Na2CO3-solution (215 ml) was degassed and Pd(Ph3P)4 (5.0 g, 0.43 mmol) was added. The reaction mixture was refluxed for 18 h and evaporated to dryness [Synlett 2000 (6), 829-831]. The residue was suspended in MeOH (215 ml), SOCl2 (15.6 ml, 215 mmol) was added dropwise at RT and the reaction mixture was refluxed for 4h. Aqueous work-up and further purification by column chromatography as described in example K4] (10.1 g, 44.4 mmol) by treatment with tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (9.50 g, 69%).

Workup

  1. customprepared by the following procedure
  2. customwas degassed
  3. temperatureThe reaction mixture was refluxed for 18 h
  4. customevaporated to dryness [Synlett 2000 (6), 829-831]
  5. temperaturethe reaction mixture was refluxed for 4h
  6. customAqueous work-up and further purification by column chromatography

Sources & evidence

ORD record
ord-aee6567072f448ceaccfd07ccf40d277
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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