Sodium Chloride → 5-(4-fluorophenyl)-1H-indole

HRID 1666795Notes

Reaction equation

HRID 1666795 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+].[Na+].[Cl-]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 249055-BromoindoleHCID 2856454-Fluorophenylboronic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 111718425-(4-fluorophenyl)-1H-indole

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Combine 5-bromoindole (5.00 g, 25.50 mmol) and Pd(Ph3P)4 (1.47 g, 1.28 mmol) in toluene (510 ml). After 30 minutes, add a solution of 4-fluorobenzeneboronic acid (5.35 g, 38.26 mmol) in ethanol (153 ml) then add saturated NaHCO3 (255 ml). Heat to reflux. After 4 hours, cool to ambient temperature, pour into saturated NaCl (250 ml), and separate the organic layer. Extract the aqueous layer with ethyl acetate. Combine the organic extracts, wash with brine, dried, then evaporate to residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexanes (10/90) to give the title compound: mp 84-89° C. MS (ACPI): m/e 212.0 (M+1). Analysis for C14H10FN: Calcd: C, 79.60; H, 4.77; N, 6.63. found: C, 79.33; H, 4.92; N, 6.64.

Workup

  1. temperatureHeat to reflux
  2. waitAfter 4 hours
  3. customseparate the organic layer
  4. extractionExtract the aqueous layer with ethyl acetate
  5. washwash with brine
  6. customdried
  7. customevaporate to residue

Sources & evidence

ORD record
ord-ac4467cc619442a5a50183f481907259
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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