Dichloromethane → HCID 68814335, compound

HRID 731103Notes

Reaction equation

HRID 731103 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[C:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=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:42]3[CH:43]=[CH:44][C:39]([O:38][CH3:37])=[CH:40][CH:41]=3)=[CH:14][CH:15]=2)[C:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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 68814191HCID 68814191, compound

Product 1

HCID 68814335HCID 68814335, 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, 1,3-dibenzyl-5-bromo-2-phenyl-1H-indole (1.932 g, 4.271 mmol) was reacted with aqueous 2M K2CO3 (4.3 ml), 4-methoxyphenylboronic acid (0.909 g, 5.979 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.105 g, 0.128 mmol) in dioxane (43 ml) to give the product (1.163 g, 2.425 mmol, 57%) as a brown, viscous oil. 1H NMR (DMSO-d6) δ 3.76 (s, 3H), 4.06 (s, 2H), 5.34 (s, 2H), 6.87 (d, J=7.6 Hz, 2H), 6.97 (d, J=8.8 Hz, 2H), 7.09-7.23 (m, 8H), 7.34 (dd, J=1.7, 8.6 Hz, 1H), 7.39-7.49 (m, 8H), 7.56 (s, 1H); [ESI(+)], m/z 480 (M+H)+.

Sources & evidence

ORD record
ord-1da256be2a56472f99b96523e3fc2271
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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