Water → HCID 46224398, compound

HRID 68139Notes

Reaction equation

HRID 68139 reaction equation
I[C:2]1[NH:3][C:4]2[C:5]([O:17][CH2:18][CH2:19][CH3:20])=[CH:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]=2[C:10](=[O:12])[CH:11]=1.[C:21](=O)([O-])[O-].[Na+].[Na+].O.[CH2:28]([CH2:31][O:32][CH3:33])OC>>[O:32]1[CH:31]=[CH:28][C:21]([C:11]2[C:10](=[O:12])[C:9]3[C:8]4[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=4[CH:6]=[C:5]([O:17][CH2:18][CH2:19][CH3:20])[C:4]=3[NH:3][CH:2]=2)=[CH:33]1

Participants

5

Reactant 4

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 674161483-iodo-5-propoxy-4H-benzo[f]quinolin-1-one

Product 1

HCID 46224398HCID 46224398, compoundYield 48%

Conditions

Temperature
95 °C

Procedure

3-Iodo-5-propoxy-4H-benzo[f]quinolin-1-one (1.06 g, 2.79 mmol) was suspended in dimethoxyethane (20 ml). Furan-3-boron acid (354 mg, 3.16 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane complex (PdCl2(DPPF).CH2Cl2, 123 mg, 0.11 mmol) and a 2N aqueous sodium carbonate solution (4.0 ml) were sequentially added to the suspension. The mixture was stirred at 90 to 100° C. under a nitrogen atmosphere for hours. The reaction mixture was cooled to room temperature, water was added thereto, and the resulting mixture was subjected to extraction using dichloromethane. The thus-obtained organic layer was concentrated under reduced pressure, and the residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=80:1). The purified product was concentrated under reduced pressure, the residue was washed with ethyl acetate and then dried, giving a pale brown powder of 2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one (430 mg, yield: 48%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe resulting mixture was subjected to extraction
  3. concentrationThe thus-obtained organic layer was concentrated under reduced pressure
  4. customthe residue was purified
  5. concentrationThe purified product was concentrated under reduced pressure
  6. washthe residue was washed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-228a7720349040428aec09930e7b044a
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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