Water → HCID 66596896, compound

HRID 1811405Notes

Reaction equation

HRID 1811405 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:18]3[C:13](=[C:14]([CH:21]4[O:25][CH2:24][CH2:23][O:22]4)[CH:15]=[CH:16][C:17]=3[O:19][CH3:20])[CH2:12][CH2:11][C:10]2=[O:26])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[S:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1.O>COCCOC.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(OCC)(=O)C>[O:22]1[CH2:23][CH2:24][O:25][CH:21]1[C:14]1[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[C:18]2[C:13]=1[CH2:12][CH2:11][C:10](=[O:26])[N:9]2[CH2:8][C:5]1[CH:6]=[N:7][C:2]([C:35]2[CH:36]=[CH:37][S:33][CH:34]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 866139171-(6-Chloropyridin-3-ylmethyl)-5-[1,3]dioxolan-2-yl-8-methoxy-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 66596896HCID 66596896, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(6-Chloropyridin-3-ylmethyl)-5-(1,3-dioxolan-2-yl)-8-methoxy-3,4-dihydro-1H-quinolin-2-one (0.4 g), tetrakis(triphenylphosphine)palladium (0.12 g) and a 2N aqueous solution of sodium carbonate (2.5 ml) were suspended in 8 ml of 1,2-dimethoxyethane, and 0.20 g of 3-thiopheneboronic acid was added, followed by heating under reflux in an argon atmosphere for 4 hours. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1). The purified product was concentrated under reduced pressure to thereby obtain 0.45 g (yield: 95%) of 5-(1,3-dioxolan-2-yl)-8-methoxy-1-(6-thiophen-3-ylpyridin-3-ylmethyl)-3,4-dihydro-1H-quinolin-2-one as a light brown amorphous solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux in an argon atmosphere for 4 hours
  3. washThe extract was washed twice with water
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
  9. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e7f75a61f014fa6aca6c77bafb9cbba
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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