Potassium → 3-(4-Pyridyl)-2-(4-fluorophenyl)indole

HRID 568166Notes

Reaction equation

[K].[F:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=O)=O)=[CH:5][CH:4]=1>C1COCC1.[Cl-].[Ti+3].[Cl-].[Cl-]>[N:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:11]3[C:10](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:9][C:7]=2[C:6]2[CH:24]=[CH:25][C:3]([F:2])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 23 °C

Procedure

Graphite (272 mg, 3.63 mmol) and potassium (100 mg, 0.33 mmol) were warmed to 150° C. under argon in a 250 mL round bottom flask with stirring for 25 min. THF (30 mL) was added via syringe to the hot bronze colored solid followed by a suspension of titanium (III) chloride (254 mg, 1.65 mmol) in THF (20 mL). The resultant black solution was allowed-to reflux for 1 h. 4-(2-(4-fluoro-N-benzoylamino)benzoyl)pyridine (14) (100 mg, 0.33 mmol) and THF (20 mL) were then added to the hot (65° C.) reaction mixture over 5 min. After 1 h at 65° C., the reaction was cooled to 23° C. the filtered through a silica gel pad (20 g). After concentration in vacuo, the residue was purified by flash chromatography (ethyl acetate:methylene chloride 1:1) to afford 3-(4-pyridyl)-2-(4-fluorophenyl)indole (3): Mass spectrum (CI) 289 (MH+).

Workup

temperatureThe resultant black solution was allowed-to reflux for 1 h
waitAfter 1 h at 65° C.
filtrationfiltered through a silica gel pad (20 g)
concentrationAfter concentration in vacuo
customthe residue was purified by flash chromatography (ethyl acetate:methylene chloride 1:1)

Sources & evidence

ORD record: ord-a5ba405895714750ae7ac03a2c383e53
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180643B2

Reaction notes

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