Dichloromethane → HCID 68814224, compound

HRID 731028Notes

Reaction equation

HRID 731028 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:5]2[CH3:18].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:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH3:11])[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]3[CH3:18])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 68813930HCID 68813930, compound

Product 1

HCID 68814224HCID 68814224, compoundYield 38%

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, 5-bromo-1,3-dimethyl-2-phenyl-1H-indole (1.358 g, 4.524 mmol) was reacted with aqueous 2M K2CO3 (4.5 ml), 4-methoxyphenylboronic acid (0.825 g, 5.429 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.074 g, 0.090 mmol) in dioxane (46 ml) to give the desired product (0.563 g, 1.719 mmol, 38%) as a white solid, mp 156-159° C. 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 3.61 (s, 3H), 3.79 (s, 3H), 7.01 (d, J=8.7 Hz, 2H), 7.43-7.50 (m, 5H), 7.55 (t, J=7.8 Hz, 2H), 7.64 (d, J=8.7 Hz, 2H), 7.73 (s, 1H); [ESI(+)], m/z 328 (M+H)+.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-6c86f5fbecd94228a9a200841c3424e0
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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