Diisopropylamine → HCID 23114746, compound

HRID 2080367Notes

Reaction equation

HRID 2080367 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1.[F:21][C:22]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=1[CH:24]=[O:25].[Cl-].[NH4+]>C(OCC)(=O)C.CCCCCC.O1CCCC1>[Cl:13][C:14]1[CH:19]=[C:18]([CH:24]([C:23]2[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:22]=2[F:21])[OH:25])[C:17]([Cl:20])=[CH:16][N:15]=1

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 276852,5-DichloropyridineHCID 1376632,5-DifluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 23114746HCID 23114746, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran solution (14 ml) of diisopropylamine (1.4 ml, 10 mmol) was added n-butyl lithium (6.3 ml, a 1.59M hexane solution) at −78° C. After stirring for 10 minutes, 2,5-dichloropyridine (1.48 g, 10 mmol) was added to the reaction mixture. Thirty minutes later, 2,5-difluorobenzaldehyde (1.09 ml, 10 mmol) was added and the temperature of the resulting mixture was raised gradually to 0° C. Stirring was conducted for further 10 minutes. After addition of an aqueous solution of ammonium chloride, the resulting mixture was diluted with ethyl acetate (80 ml). The organic layer was separated, washed with brine and then dried. After filtration, the precipitate obtained by concentrating the filtrate under reduced pressure was triturated with ethanol to give the title compound (1.93 g, 67%).

Workup

  1. customat −78° C
  2. stirringStirring
  3. waitwas conducted for further 10 minutes
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. filtrationAfter filtration
  8. customthe precipitate obtained
  9. concentrationby concentrating the filtrate under reduced pressure
  10. customwas triturated with ethanol

Sources & evidence

ORD record
ord-ec061c5ad5a2481da7cbe547f25e05cb
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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