Dichloromethane → HCID 68814959, compound

HRID 731061Notes

Reaction equation

HRID 731061 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[N:10]([CH3:18])[C:9]=1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=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]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[CH:15]=2)[N:10]([CH3:18])[C:9]=1[CH3:19])[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 688139383-Benzyl-5-bromo-1,2-dimethyl-1H-indole

Product 1

HCID 68814959HCID 68814959, 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, 3-benzyl-5-bromo-1,2-dimethyl-1H-indole (1.453 g, 4.624 mmol) was reacted with aqueous 2M K2CO3 (4.6 ml), 4-methoxyphenylboronic acid (0.843 g, 5.549 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.076 g, 0.092 mmol) in dioxane (46 ml) to give the product (0.419 g, 1.227 mmol, 27%) as a solid, mp 139-141° C. 1H NMR (DMSO-d6) δ 2.40 (s, 3H), 3.67 (s, 3H), 3.76 (s, 3H), 4.06 (s, 2H), 6.97 (d, J=8.9 Hz, 2H), 7.08-7.12 (m, 1H), 7.19-7.24 (m, 4H), 7.29 (dd, J=1.8, 8.6 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.51 (d, J=8.9 Hz, 2H), 7.55 (d, J=1.5 Hz, 1H); [ESI(+)], m/z 342 (M+H)+.

Sources & evidence

ORD record
ord-515e01462b96477c8c4dc48dc862655c
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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