Water → HCID 21914412, compound

HRID 2378540Notes

Reaction equation

HRID 2378540 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.Br[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.O>C1COCC1.C(OCC)(=O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([O:13][CH2:12][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 693532,5-DibromopyridineHCID 77195CyclopentanemethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 21914412HCID 21914412, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of potassium t-butoxide (550.6 mg, WAKO) in dehydrated THF (10 ml) was added with cyclopentane methanol (450 μl), and then added with a solution of 2,5-dibromopyridine (982.8 mg, TCI) in dehydrated THF (15 ml) under ice cooling. The reaction mixture was stirred for 30 minutes, then warmed to room temperature, and stirred for 11 hours. The reaction mixture was added with water (100 ml) and ethyl acetate (60 ml) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine sequentially, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=15:1) to obtain the title compound (Intermediate 28, 896 mg).

Workup

  1. stirringstirred for 11 hours
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine sequentially
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-e3eb2071b3764fbeb5ca72d73799014d
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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