Acetone → HCID 86585287, compound

HRID 2304762Notes

Reaction equation

HRID 2304762 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:6]([N:19]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH:20]=[O:21])=[C:5]2[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Li]CCCC.[CH3:41][C:42]([CH3:44])=[O:43].[NH4+].[Cl-]>C1COCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:42]([OH:43])([CH3:44])[CH3:41])=[CH:10][CH:9]=3)[C:5]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[C:6]2[N:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[O:21])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 86585286HCID 86585286, compoundHCID 178418339Butyllithium

Product 1

HCID 86585287HCID 86585287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

To a solution of 201 mg of {5-Bromo-1-[(4-fluorophenyl)methyl]-3-(phenylmethoxy)indol-2-yl}-N-(3-pyridyl)formamide in 10 mL of THF at −100° C. was added 0.5 mL of n-BuLi (1.6 M in hexanes) and the mixture was stirred at −100° C. for 30 min. To this cold solution, 190 μL of acetone was added and the reaction mixture was allowed to warm to room temperature. At this time, aqueous NH4Cl was added, the product was extracted with ethyl acetate and the organic phase was washed with brine and dried over anhydrous Na2SO4. Flash chromatography (100% hexane to hexane/ethyl acetate 1:2) and swish with CH2Cl2/hexane yielded 61 mg of the title compound as a yellow solid.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe product was extracted with ethyl acetate
  3. washthe organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-8b3e629baedf4a26a9d925f772ed9d44
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

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