Dichloromethane → 2-Cyano-1-(4-fluorobenzyl)-5-methanesulfonylindole

HRID 1814101

Reaction equation

HRID 1814101 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]([NH2:22])=O)=[CH:4][CH:3]=1.ClCCl.C(N(CC)CC)C.FC(F)(F)C(O)=O>O>[C:20]([C:8]1[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][C:12]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=2)#[N:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 225043691-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carboxamide

Product 1

HCID 225044482-Cyano-1-(4-fluorobenzyl)-5-methanesulfonylindoleYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxamide (100 mg) and dichloromethane (2 ml), triethylamine (0.09 ml) and anhydrous trifluoroacetic acid (0.09 ml) were added at 15 to 30° C. and the mixture was stirred at the same temperature for 2 hours. Water was added therto, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 68 mg of the desired product as a white crystal.

Workup

  1. additionwere added at 15 to 30° C.
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-768ae26247fa44bdbc9924daf81bc145
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Linked notes

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