Dichloromethane → HCID 68813801, compound

HRID 731096Notes

Reaction equation

HRID 731096 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[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C([O-])([O-])=O.[K+].[K+].[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=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]>[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([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[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 68814792HCID 68814792, compound

Product 1

HCID 68813801HCID 68813801, 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, 5-bromo-1-methyl-3-pentyl-2-phenyl-1H-indole (1.105 g, 3.101 mmol) was reacted with aqueous 2M K2CO3 (3.1 ml), 4-methoxyphenylboronic acid (0.660 g, 4.341 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.076 g, 0.093 mmol) in dioxane (31 ml) to give the product (0.512 g, 1.335 mmol, 43%) as an oily solid. 1H NMR (DMSO-d6) δ 0.76 (t, J=6.9 Hz, 3H), 1.15-1.23 (m, 4H), 1.52-1.56 (m, 2H), 2.66 (t, J=7.5 Hz, 2H), 3.56 (s, 3H), 3.79 (s, 3H), 7.02 (d, J=8.7 Hz, 2H), 7.41-7.46 (m, 3H), 7.47-7.49 (m, 2H), 7.53-7.56 (m, 2H), 7.61 (d, J=8.6 Hz, 2H), 7.72 (d, J=1.5 Hz, 1H); [ESI(+)], m/z 384 (M+H)+.

Sources & evidence

ORD record
ord-085817c570c1498796e222e340eff648
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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