Tetrahydrofuran → HCID 59323160, compound

HRID 2390030Notes

Reaction equation

HRID 2390030 reaction equation
CON(C)[C:4]([CH2:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=O.Br[C:19]1[CH:24]=[CH:23][CH:22]=C[C:20]=1[Cl:25].CN(CCN(C)C)C.[Li]CCCC.[Cl-].[NH4+].C1C[O:44]CC1>>[Cl:25][C:20]1[CH:19]=[CH:24][CH:23]=[CH:22][C:4]=1[C:6]([C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:44]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 127541-Bromo-2-chlorobenzeneHCID 25517Ammonium ChlorideHCID 131729961HCID 131729961, compoundHCID 178418339Butyllithium

Product 1

HCID 59323160HCID 59323160, compoundYield 65%

Procedure

Under an argon atmosphere, to a solution of 120 mg of N-methoxy-N-methyl isoquinoline-3-carboxyamide obtained in Example 1-a), 159 mg of 2-bromochlorobenzene, and 0.14 mL of TMEDA in 3 mL of THF was added portionwise a BuLi (1.57 M) solution at −78° C. The reaction liquid was stirred at the same temperature for 10 minutes, and further stirred for 1 hour under ice-cooling. After completion of the reaction, to the reaction liquid were added ice water and ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation to obtain 171 mg of a crude composition. This was purified by PLC (hexane:ethyl acetate=1:1) to obtain 97 mg (yield 65%) of a title compound as a yellow oily substance.

Workup

  1. customThe reaction liquid
  2. stirringfurther stirred for 1 hour under ice-
  3. temperaturecooling
  4. customAfter completion of the reaction
  5. customto the reaction liquid
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed by evaporation
  10. customto obtain 171 mg of a crude composition
  11. customThis was purified by PLC (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-90e74f6abeb445f99d9e4199228f23db
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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