Chlorosuccinimide → HCID 15290722, compound

HRID 2259504Notes

Reaction equation

HRID 2259504 reaction equation
[F:1][C:2]1[S:10][C:9]2[C:4](=[N:5][C:6]([CH3:11])=[CH:7][CH:8]=2)[CH:3]=1.C([Li])CCC.[Cl:17]N1C(=O)CCC1=O>C1COCC1.C(NC(C)C)(C)C>[Cl:17][C:3]1[C:4]2=[N:5][C:6]([CH3:11])=[CH:7][CH:8]=[C:9]2[S:10][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 15290719HCID 15290719, compoundHCID 178418339Butyllithium

Product 1

HCID 15290722HCID 15290722, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 7912DiisopropylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 461 mg (2.74 mmol) of 2-fluoro-5-methylthieno [3.2-b]pyridine (Example 7, Step 1) and 14 μl (0.1 mmol) of diisopropylamine in 12 mL of THF was added 2.15 mL of n-butyl lithium (1.4M in hexane) at -78° C. After stirring at -78° C. for 10 min, a solution of 585 mg (4.4 mmol) of N-chlorosuccinimide in 10 mL of THF was added at -78° C. The mixture was stirred at -78° C. for 20 min, warmed up to 0° C., stirred at 0° C. for 30 min, and then partitioned between aqueous ammonium chloride and ethyl acetate. Chromatographic purification on silica gel with hexane/ethyl acetate=8:1 gave 350 mg (63%) of the title product.

Workup

  1. stirringThe mixture was stirred at -78° C. for 20 min
  2. temperaturewarmed up to 0° C.
  3. stirringstirred at 0° C. for 30 min
  4. custompartitioned between aqueous ammonium chloride and ethyl acetate
  5. customChromatographic purification on silica gel with hexane/ethyl acetate=8:1

Sources & evidence

ORD record
ord-382795b2cdfc40548ca974ee12cf6b01
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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