Dichloromethane → HCID 68815374, compound

HRID 731082Notes

Reaction equation

HRID 731082 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:18])=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:6]2[CH3:11].C([O-])([O-])=O.[K+].[K+].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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]>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]([CH3:18])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]3[CH3:11])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 68814415HCID 68814415, compound

Product 1

HCID 68815374HCID 68815374, 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, 4-bromo-1,3-dimethyl-2-phenyl-1H-indole (1.182 g, 3.937 mmol) was reacted with aqueous 2M K2CO3 (3.9 ml), 4-methoxyphenylboronic acid (0.838 g, 5.512 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.096 g, 0.118 mmol) in dioxane (39 ml) to give the product (1.253 g, 3.827 mmol, 97%) as a yellow, viscous oil. 1H NMR (DMSO-d6) δ 1.72 (s, 3H), 3.60 (s, 3H), 3.81 (s, 3H), 6.85 (dd, J=0.8, 7.0 Hz, 1H), 6.99 (d, J=8.7 Hz, 2H), 7.20 (t, J=7.3 Hz, 1H), 7.32 (d, J=8.7 Hz, 2H), 7.41-7.47 (m, 4H), 7.53 (t, J=7.6 Hz, 2H); [ESI(+)], m/z 328 (M+H)+.

Sources & evidence

ORD record
ord-968077798e60425d865b9b7c27f8aa12
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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