Diisopropylamine → HCID 19002844, compound

HRID 2259501Notes

Reaction equation

HRID 2259501 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][S:10][C:5]2=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[Li]CCCC.[Cl:23]N1C(=O)CCC1=O.[NH4+].[Cl-]>C1COCC1>[Cl:23][C:9]1[S:10][C:5]2[C:6](=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:8]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 591057HCID 591057, compoundHCID 178418339Butyllithium

Product 1

HCID 19002844HCID 19002844, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution 5-methylthieno[3,2-b]pyridine (3.60 g, 24 mmol) and N,N-diisopropylamine (100 uL) in THF (80 mL) at -78° C. was added dropwise 16 mL of n-BuLi (1.6M, 25.6 mmol). The mixture was stirred at -78° C. for 20 min and then transfered via a cannula to a solution of N-chlorosuccinimide (4.5 g, 34 mmol) in THF (300 mL) at -10° C. The mixture was stirred at -10° C. for 30 min. Saturated NH4Cl solution was then added and the product was extracted with EtOAc, dried over MgSO4, and concentrated to an oil. Chromatography of the crude oil on silica gel (eluted with 15% EtOAc in hexane) yielded 3.60 g (81%) of the title compound.

Workup

  1. stirringThe mixture was stirred at -10° C. for 30 min
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-f75cf5f316c645eb904deef0ba4a79b7
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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