Indole → HCID 12000289, compound

HRID 2113184Notes

Reaction equation

HRID 2113184 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.F[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O.O>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 99931-Bromo-4-fluorobenzeneHCID 2855718-Crown-6HCID 522689Potassium Fluoride

Product 1

HCID 12000289HCID 12000289, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1H-indole (3.0 g, 25.6 mmol), 4-fluorobromobenzene (4.48 g, 25.6 mmol), potassium fluoride (40% wt on alumina; 3.0 g) and 18-crown-6 (690 mg, 2.56 mmol) in anhydrous DMSO (30 mL) was heated at 150° C. for 24 hours, and then cooled to room temperature. The reaction mixture was poured into water (50 mL) and extracted with diethyl ether (3×50 mL). The combined organic extract was washed with water (2×30 mL), brine (3×30 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 20% ethyl acetate/hexane as eluent, afforded the title compound has a pale yellow solid (5.5 g, 76%).

Workup

  1. extractionextracted with diethyl ether (3×50 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water (2×30 mL), brine (3×30 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-cf187a71463b47f8944b9607005fec0a
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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