Dichloromethane → 9-Benzyl-6-(4-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-carbazole

HRID 731042Notes

Reaction equation

HRID 731042 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12](Br)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=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:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([C:33]1[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1)[CH:13]=2)[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 688159639-Benzyl-6-bromo-2,3,4,9-tetrahydro-1H-carbazole

Product 1

HCID 688167799-Benzyl-6-(4-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-carbazole

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, 9-benzyl-6-bromo-2,3,4,9-tetrahydro-1H-carbazole (2.217 g, 6.516 mmol) was reacted with aqueous 2M K2CO3 (6.5 ml), 4-methoxyphenylboronic acid (1.188 g, 7.819 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.106 g, 0.130 mmol) in dioxane (65 ml) to give the product (1.94 g, 5.28 mmol, 81%) as a viscous brown oil. 1H NMR (DMSO-d6) δ 1.79-1.86 (m, 4H), 2.63-2.71 (m, 4H), 3.78 (s, 3H), 5.33 (s, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.03 (d, J=7.5 Hz, 2H), 7.21 (t, J=7.0 Hz, 1H), 7.25-7.30 (m, 3H), 7.38 (d, J=8.6 Hz, 1H), 7.56-7.58 (m, 3H); [ESI(+)], m/z 368 (M+H)+.

Sources & evidence

ORD record
ord-c5853f1499fc4990a57054e672f138f1
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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