Dichloromethane → HCID 68815903, compound

HRID 731054Notes

Reaction equation

HRID 731054 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][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=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:37]3[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=3)=[CH:14][CH:15]=2)[C:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]1[CH3:25])[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 688151801,3-Dibenzyl-5-bromo-2-methyl-1H-indole

Product 1

HCID 68815903HCID 68815903, compound

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, 1,3-dibenzyl-5-bromo-2-methyl-1H-indole (1.842 g, 6.133 mmol) was reacted with aqueous 2M K2CO3 (6.1 ml), 4-methoxyphenylboronic acid (1.118 g, 7.360 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.100 g, 0.123 mmol) in dioxane (61 ml) to give the product (0.702 g, 1.681 mmol, 27%) as a pale-yellow solid, mp 136-139° C. 1H NMR (DMSO-d6) δ 2.35 (s, 3H), 3.76 (s, 3H), 4.10 (s, 2H), 5.43 (s, 2H), 6.95-7.00 (m, 4H), 7.09-7.13 (m, 1H), 7.20-7.30 (m, 8H), 7.39 (d, J=8.6 Hz, 1H), 7.48-7.51 (m, 2H), 7.57 (d, J=1.5 Hz, 1H); [ESI(+)], m/z 418 (M+H)+.

Sources & evidence

ORD record
ord-874a76e264a347bba3cdfea8d0053bcf
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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