Dichloromethane → HCID 68814367, compound

HRID 731068Notes

Reaction equation

HRID 731068 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[C:10]([CH3:18])=[C:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=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][CH:13]=[C:14]([C:36]3[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][CH:35]=3)[CH:15]=2)[C:10]([CH3:18])=[C:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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 68816825HCID 68816825, compound

Product 1

HCID 68814367HCID 68814367, 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-benzyl-6-bromo-3-methyl-2-phenyl-1H-indole (1.432 g, 3.805 mmol) was reacted with aqueous 2M K2CO3 (3.8 ml), 4-methoxyphenylboronic acid (0.809 g, 5.327 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.093 g, 0.114 mmol) in dioxane (38 ml) to give the product (1.017 g, 2.861 mmol, 75%) as a white solid, mp 142-145° C. 1H NMR (DMSO-d6) δ 2.23 (s, 3H), 3.77 (s, 3H), 5.39 (s, 2H), 6.86 (d, J=7.0 Hz, 2H), 6.98 (d, J=8.9 Hz, 2H), 7.13 (t, J=7.3 Hz, 1H), 7.18 (t, J=7.0 Hz, 2H), 7.34 (dd, J=1.5, 7.8 Hz, 1H), 7.38-7.44 (m, 3H), 7.48 (t, J=7.0 Hz, 2H), 7.55-7.61 (m, 4H); [ESI(+)], m/z 404 (M+H)+.

Sources & evidence

ORD record
ord-83fe788702e4451f931c1e62e3a70f56
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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