Dichloromethane → HCID 22032917, compound

HRID 1791437Notes

Reaction equation

HRID 1791437 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]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:25]3[CH:26]=[CH:27][C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:23][CH:24]=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

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2857561-Benzyl-5-Bromo-1H-IndoleHCID 27343204-tert-Butylphenylboronic acid

Product 1

HCID 22032917HCID 22032917, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

-Benzyl-5-[4-(tert-butyl)phenyl]-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (1.44 g, 5.03 mmol), and 4-(tert-butyl)phenylboronic acid (1.08 g, 6.07 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.204 g, 0.250 mmol), and potassium carbonate (1.39 g, 10.1 mmol) in dioxane (50 mL) and water (5 mL) following the procedure described in Step 1 of Example 11. Purification by flash chromatography (Biotage apparatus) using 0-5% chloroform in hexane as an eluant yielded the title compound as an aqua solid (0.741 g, 43%), mp: 136-137° C. 1HNMR (200 MHz, DMSO-d6): δ 7.8 (s, 1H), 7.2-7.6 (m, 12H), 6.55 (d, 1H, J=2.6 Hz), 5.45 (s, 2H), and 1.3 ppm (s, 9H).

Workup

  1. custom-Benzyl-5-[4-(tert-butyl)phenyl]-1H-indole was prepared
  2. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-a5590bbaca1c49449801de188a82774f
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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