Morpholine → HCID 67382101, compound

HRID 909343Notes

Reaction equation

HRID 909343 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[NH:78]1[CH2:83][CH2:82][O:81][CH2:80][CH2:79]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].C1(C)C=CC=CC=1>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([N:78]4[CH2:83][CH2:82][O:81][CH2:80][CH2:79]4)=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:12]=1)[CH3:25]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 67382101HCID 67382101, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

7-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (1.0 g), (+)-2,2′-bis(diphenylphosphino)-1,1′binaphthyl (BINAP, 0.089 g), tris(dibenzylideneacetone)dipalladium(0) (0.074 g), sodium tert-butoxide (0.320 g,), morpholine (0.230 mL,) and toluene (4.8 mL) were added to a scintillation vial. The vial was sequentially flushed with nitrogen, sealed with a Teflon-lined cap, placed in an oil bath, and heated at 80° C. for 16 hours. The reaction mixture was cooled to ambient temperature and then transferred to a round bottom flask. The volatiles were removed under reduced pressure and the residue was purified by column chromatography on a Biotage Horizon™ High Performance Flash Chromatography instrument using a silica gel cartridge. The purification was carried out eluting with chloroform:CMA in a gradient from 98:2 to 75:25. 2-Ethoxymethyl-1-(3-isopropoxypropyl)-7-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline was isolated as a red-orange oil (1.32 g).

Workup

  1. customThe vial was sequentially flushed with nitrogen
  2. customsealed with a Teflon-
  3. customlined cap
  4. customplaced in an oil bath
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. customtransferred to a round bottom flask
  7. customThe volatiles were removed under reduced pressure
  8. customthe residue was purified by column chromatography on a Biotage Horizon™ High Performance Flash Chromatography instrument
  9. customThe purification
  10. washwas carried out eluting with chloroform

Sources & evidence

ORD record
ord-24e1ec99f7604883b0596b79a7fc1d11
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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