Diisopropylamine → HCID 23503601, compound

HRID 1835429Notes

Reaction equation

HRID 1835429 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=1.[CH3:21][O:22][C:23]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:24]=1[CH:25]=[O:26]>O.C1(C)C=CC=CC=1.C(OCC)C>[CH3:21][O:22][C:23]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:24]=1[CH:25]([C:19]1[C:18]([Br:20])=[CH:17][N:16]=[CH:15][C:14]=1[Br:13])[OH:26]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 693693,5-DibromopyridineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 23503601HCID 23503601, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

57.0 ml (88.9 mmol) of n-butyllithium (1.56 M hexane solution) was dropwise added to a diethyl ether (110 ml) solution of 12.5 ml (89.2 mmol) of diisopropylamine at 0° C., followed by stirring for 60 minutes. The solution was cooled to −78° C., a toluene (80 ml) solution of 20 g (85 mmol) of 3,5-dibromopyridine was added thereto, followed by stirring for 5 minutes, and then a toluene 50 ml solution of 21.0 g (100 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde was added thereto, followed by stirring for 2 hours. 50 ml of water was added to the mixture to terminate the reaction, the aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 11.8 g (yield 31%) of (2,3,4-trimethoxy-6-methylphenyl)(3,5-dibromo-4-pyridyl)methanol (yellow oily substance).

Workup

  1. stirringby stirring for 5 minutes
  2. stirringby stirring for 2 hours
  3. customto terminate
  4. customthe reaction
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product thus obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc1651433c4a48638d8a1a137f4ae288
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

Loading…