Diisopropylamine → HCID 23114746, compound

HRID 748839Notes

Reaction equation

HRID 748839 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.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

8

Reactant 5

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

Product 1

HCID 23114746HCID 23114746, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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, 1.59M hexane solution) at −78° C. After stirring for 10 minutes, 2,5-dichloropyridine (1.48 g, 10 mmol) was added. Thirty minutes later, 2,5-difluorobenzaldehyde (1.09 ml, 10 mmol) was added to the mixture. The resulting mixture was warmed gradually to 0° C. and stirring was conducted for further 10 minutes. An aqueous solution of ammonium chloride was added and the mixture was diluted with ethyl acetate (80 ml). The organic layer was separated, washed with brine and dried. After filtration, the filtrate was concentrated under reduced pressure. The precipitate thus obtained was triturated with ethanol to yield the title compound (1.93 g, 67%).

Workup

  1. stirringstirring
  2. waitwas conducted for further 10 minutes
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe precipitate thus obtained
  9. customwas triturated with ethanol

Sources & evidence

ORD record
ord-9e730c39d3c44fc0b1827d6986cabdb2
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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