Dichloromethane → HCID 68814868, compound

HRID 731034Notes

Reaction equation

HRID 731034 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[C: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]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)=[CH:14][CH:15]=2)[C: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 252288201-Benzyl-5-bromo-2,3-dimethyl-1H-indole

Product 1

HCID 68814868HCID 68814868, 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-5-bromo-2,3-dimethyl-1H-indole (1.872 g, 5.958 mmol) was reacted with aqueous 2M K2CO3 (6.0 ml), 4-methoxyphenylboronic acid (1.087 g, 7.150 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.097 g, 0.119 mmol) in dioxane (60 ml) to give the product (0.925 g, 2.709 mmol, 45%) as a brown oil. 1H NMR (DMSO-d6) δ 2.24 (s, 3H), 2.28 (s, 3H), 3.78 (s, 3H), 5.39 (s, 2H), 6.97-6.99 (m, 4H), 7.20 (t, J=7.2 Hz, 1H), 7.25-7.29 (m, 3H), 7.37 (d, J=8.4 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.61 (s, 1H); [ESI(+)], m/z 342 (M+H)+.

Sources & evidence

ORD record
ord-28443fab889e483f8c7fe7e715e4c4fc
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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