Dichloromethane → HCID 68814892, compound

HRID 731110Notes

Reaction equation

HRID 731110 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[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:25]([O-:28])([O-])=O.[K+].[K+].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:2]3[CH:7]=[CH:6][C:5]([O:28][CH3:25])=[CH:4][CH:3]=3)[CH:15]=2)[N: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

6

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 68815678HCID 68815678, compound

Product 1

HCID 68814892HCID 68814892, 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-methyl-2-phenyl-1H-indole (1.525 g, 4.053 mmol) was reacted with aqueous 2M K2CO3 (4.1 ml), 4-methoxyphenylboronic acid (0.862 g, 5.674 mmol) [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.099 g, 0.122 mmol) in dioxane (41 ml) to give the product (0.766 g, 1.898 mmol, 47%) as an off-white solid, mp 122-125° C. 1H NMR (DMSO-d6) δ 3.62 (s, 3H), 3.77 (s, 3H), 4.04 (s, 2H), 6.98 (d, J=8.6 Hz, 2H), 7.07-7.11 (m, 3H), 7.18 (t, J=7.8 Hz, 2H), 7.42 (dd, J=1.5, 8.6 Hz, 1H), 7.45-7.55 (m, 9H); [ESI(+)], m/z 405 (M+H)+.

Sources & evidence

ORD record
ord-7f5f7a07f26a4733a7835ef6fc05aee3
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

Loading…