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Ethyl 2-aminobenzoate → Ethyl acetate hexane

HRID 42070
Notes
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Reaction equation

HRID 42070 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:6][CH:7]=1.[NH2:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:8].[C:19]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:18].[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH:16][C:17]3[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=3[C:19]([OH:21])=[O:20])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6877Ethyl 2-aminobenzoate2×HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 497585195-Bromo-2-(3-methoxyphenyl)pyridine2×

Product 2

HCID 21226206Ethyl acetate hexaneYield 98.4%
HCID 25186999
2-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acid

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.

Workup

  1. customThe solvent was evaporated
  2. customthe solid residue was triturated with aqueous solution of 2N HCl
  3. extractionextracted with CHCl3

Sources & evidence

ORD record
ord-0c6010783c884be28f919b4217d37301
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536165B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes