1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate (Fluorinating Reagent) → 1-cyclopropylmethyl-6-ethoxy-3-fluoro-2-(4-nitro-phenyl)-1H-indole

HRID 502273Notes

Reaction equation

HRID 502273 reaction equation
[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)[CH:7]=[C:6]2[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:3][CH2:2]1.[F:26][B-](F)(F)F.F[N+]1C(C)=CC(C)=CC=1C>C(Cl)Cl>[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)[C:7]([F:26])=[C:6]2[C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 27793091-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate (Fluorinating Reagent)HCID 590304261-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole

Product 1

HCID 590304331-cyclopropylmethyl-6-ethoxy-3-fluoro-2-(4-nitro-phenyl)-1H-indoleYield 25.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (600 mg, 1.79 mmol) in CH2Cl2 (4 mL) was added 1-fluoro-2,4,6-trimethyl pyridinium tetrafluoroborate (418 mg, 1.85 mmol). The reaction mixture was stirred at room temperature for 3 days and then diluted in CH2Cl2 and washed with aq. NaHCO3. The organic layer was dried, concentrated and purified by silica gel chromatography (1:1 CH2Cl2/hexane) to provide 1-cyclopropylmethyl-6-ethoxy-3-fluoro-2-(4-nitro-phenyl)-1H-indole (161 mg, 25%) as a yellow solid.

Workup

  1. washwashed with aq. NaHCO3
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (1:1 CH2Cl2/hexane)

Sources & evidence

ORD record
ord-c543ef66d1ea438387d5b731a859fbb7
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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