Sodium Bicarbonate → 6-Chloro-2-oxo-4-pent-1-enyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1745859Notes

Reaction equation

HRID 1745859 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:34])[N:8](CC2C=CC(OC)=CC=2)[C:9]2[C:14]([C:15]=1OS(C(F)(F)F)(=O)=O)=[CH:13][C:12]([Cl:24])=[CH:11][CH:10]=2)=[O:5])[CH3:2].[CH:35](/B(O)O)=[CH:36]\[CH2:37][CH2:38][CH3:39].C([O-])(O)=O.[Na+].COCCOC.O>O.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>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:34])[NH:8][C:9]2[C:14]([C:15]=1[CH:35]=[CH:36][CH2:37][CH2:38][CH3:39])=[CH:13][C:12]([Cl:24])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5702651(1E)-(Pent-1-en-1-yl)boronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 210202526-Chloro-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 696592886-Chloro-2-oxo-4-pent-1-enyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl esterYield 70.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A solution of 11 (0.10 g, 0.19 mmol), E-penten-1-ylboronic acid (44.0 mg, 0.38 mmol), tetrakis(triphenylphosphine)palladium (22.0 mg, 0.023 mmol), and NaHCO3 (41.0 mg, 0.38 mmol) in 1:1 DME/H2O (3 mL) was heated at 100° C. for 1 h. The reaction was allowed to cool to room temperature, diluted with H2O, extracted with EtOAc, dried (Na2SO4), filtered, and concentrated. Chromatography (SiO2, 3:1 Hex/EtOAc) gave 12 (43.0 mg, 51%) as a colorless film.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7849a97140740f0b243db2fa0970248
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

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