Dichloromethane → 1-Benzyl-5-phenyl-1H-indole

HRID 2221239Notes

Reaction equation

HRID 2221239 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 2857561-Benzyl-5-Bromo-1H-Indole

Product 1

HCID 220329371-Benzyl-5-phenyl-1H-indoleYield 35%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Benzyl-5-phenyl-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (2.72 g, 9.50 mmol), and phenylboronic acid (1.39 g, 11.4 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.266 g, 0.326 mmol), and potassium carbonate (2.06 g, 14.9 mmol) in dioxane (72 mL) and water (7.2 mL), following the procedure described in Step 1 of Example 11. Purification by flash chromatography (Biotage apparatus) using hexane as an eluant yielded the title compound as a light yellow solid (0.928 g, 35%), mp: 105-106° C. Mass spectrum (+ES, [M+H]+) m/z 284; 1HNMR (500 MHz, DMSO-d6): δ 7.8 (d, 1H, J=0.92 Hz), 7.65 (dd, 2H, J=8.2 Hz and 0.84 Hz), 7.5-7.55 (m, 2H), 7.35-7.45 (m, 3H), 7.2-7.3 (m, 6H), 6.55 (dd, 1H, J=3.1 Hz and 0.61 Hz), and 5.45 ppm (s, 2H).

Workup

  1. custom1-Benzyl-5-phenyl-1H-indole was prepared
  2. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-2e2faf59e0bc483395595cb94e4365a4
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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