Dichloromethane → 1-Benzyl-5-(4-methoxy-phenyl)-3-pentyl-2-phenyl-1H-indole

HRID 731089Notes

Reaction equation

HRID 731089 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:35][O:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.ClCCl>O1CCOCC1.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:40]3[CH:41]=[CH:42][C:37]([O:36][CH3:35])=[CH:38][CH:39]=3)=[CH:14][CH:15]=2)[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 688139541-Benzyl-5-bromo-3-pentyl-2-phenyl-1H-indole

Product 1

HCID 688143491-Benzyl-5-(4-methoxy-phenyl)-3-pentyl-2-phenyl-1H-indole

Reagents, catalysts & solvents 2

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

Procedure

The desired product was prepared using a procedure similar to step 3 of example 3. Thus, 1-benzyl-5-bromo-3-pentyl-2-phenyl-1H-indole (1.282 g, 2.965 mmol) was reacted with aqueous 2M K2CO3 (3.0 ml), 4-methoxyphenylboronic acid (0.631 g, 4.151 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.073 g, 0.089 mmol) in dioxane (30 ml) to give the product (0.727 g, 1.582 mmol, 53%) as a yellow solid, mp 91-110° C. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.15-1.21 (m, 4H), 1.54-1.59 (m, 2H), 2.68 (t, J=7.3 Hz, 2H), 3.79 (s, 3H), 5.27 (s, 2H), 6.84 (d, J=7.0 Hz, 2H), 7.01 (d, J=8.9 Hz, 2H), 7.15 (t, J=7.2 Hz, 1H), 7.20 (t, J=6.9 Hz, 2H), 7.33-7.38 (m, 4H), 7.43 (t, J=7.2 Hz, 1H), 7.48 (t, J=6.9 Hz, 2H), 7.60 (d, J=8.9 Hz, 2H), 7.75 (d, J=0.8 Hz, 1H); [ESI(+)], m/z 460 (M+H)+.

Sources & evidence

ORD record
ord-558832d65d03424da42c418905fb886a
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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