Diethylamine → HCID 18398657, compound

HRID 1018962Notes

Reaction equation

HRID 1018962 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:11]=1)[N:8]=[C:7]([CH3:20])[CH:6]=[CH:5]2.[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(CC)CC.C([O-])(O)=O.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:11]=2)[N:8]=[C:7]([CH3:20])[CH:6]=[CH:5]3)=[CH:25][CH:24]=1

Participants

9

Reactant 5

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 18398676HCID 18398676, compound

Product 1

HCID 18398657HCID 18398657, compoundYield 79.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a degassed solution of diethyl 6-bromo-2-methyl-8-quinolylphosphonate (429 mg, 1.2 mmol, obtained from step 1) and 4-hydroxymethylphenylboronic acid (364 mg, 2.4 mmol) in toluene (6 mL) was added Pd2(dba)3 (54.9 mg, 0.06 mmol). The mixture was degassed and Ph3P (125 mg, 0.48 mmol), Et2NH (105 mg, 1.44 mmol), n-propanaol (0.9 mL) and H2O (0.9 m-L) was added. The mixture was heated to reflux for 6 h. Aqueous NaHCO3 was added and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 369 mg (79%) of the title compound.

Workup

  1. customThe mixture was degassed
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 6 h
  4. extractionthe resulting mixture was extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (anhyd. MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-200ef2d4eeca45dc942c12458a8700e0
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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