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Methyl 2-bromobenzoate → Methyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-oxopropyl)benzoate

HRID 326930
Notes
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Reaction equation

HRID 326930 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([OH:23])[CH:21]=[CH2:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[Li]OC(C)=O.[Li+].[Cl-].Br[C:32]1[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=1[C:34]([O:36][CH3:37])=[O:35]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:20](=[O:23])[CH2:21][CH2:22][C:32]4[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=4[C:34]([O:36][CH3:37])=[O:35])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11894Methyl 2-bromobenzoateHCID 433294Lithium ChlorideHCID 534062851-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-olHCID 178506943lithium acetate

Product 1

HCID 53394881Methyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-oxopropyl)benzoateYield 92.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A degassed suspension of 1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-ol (Example 80, Step 1, 50.30 g, 156 mmol), LiOAc/2H2O (41.2 g, 404 mmol), LiCl (6.84 g, 161 mmol), Pd(OAc)2 (1.00 g, 4.45 mmol) and methyl 2-bromobenzoate (33.5 g, 156 mmol) in 300 mL of DMF was stirred at 95° C. for 4 h. The mixture was cooled to r.t (room temperature) and added to 1.8 L of water. The product was extracted with hot EtOAc, dried over Na2SO4 and concentrated. It was dissolved in toluene and filtered through silica with toluene. Recrystallization in 1.2 L of EtOAc: hexanes 1:1 afforded 65.57 g of the title compound. Recrystallization of the mother liquors in 400 mL EtOAc:hexanes 1:3 afforded a further 8.30 g (86% overall yield) of the title material.

Workup

  1. temperatureThe mixture was cooled to r.t (room temperature)
  2. extractionThe product was extracted with hot EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. dissolutionIt was dissolved in toluene
  6. filtrationfiltered through silica with toluene
  7. customRecrystallization in 1.2 L of EtOAc: hexanes 1:1

Sources & evidence

ORD record
ord-9645b1aa6e524d88ae2906a580f2f72c
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05270324

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes