Dichloromethane → HCID 22032907, compound

HRID 1791450Notes

Reaction equation

HRID 1791450 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2Br)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[F:25].ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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][CH:13]=[CH:14][C:15]=2[C:21]2[CH:22]=[CH:23][C:24]([F:25])=[C:19]([Cl:18])[CH:20]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 10613176HCID 10613176, compound

Product 1

HCID 22032907HCID 22032907, compoundYield 23.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Benzyl-7-(3-chloro-4-fluorophenyl)-1H-indole was prepared by coupling 1-benzyl-7-bromo-1H-indole (0.691 g, 2.41 mmol), and 3-chloro-4-fluorophenylboronic acid (0.538 g, 3.09 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0628 g, 0.0769 mmol), and potassium carbonate (0.502 g, 3.63 mmol) in dioxane (18 mL) and water (1.8 mL) following the procedure described in Step 1 of Example 11. Purification by HPLC using 1.5% ethyl acetate in hexane as the mobile phase furnished the title compound as a clear gum (0.189 g, 23%). 1HNMR (300 MHz, DMSO-d6): δ 7.65 (d, 1H, J=7.5 Hz), 7.5 (s, 1H), 7.3 (t, 1H, J=8.3 Hz), 7.05-7.2 (m, 6H), 6.85 (d, 1H, J=7.5 Hz), 6.65 (d, 1H, J=3.8 Hz), 6.3-6.4 (m, 2H), and 4.95-5.2 ppm (m, 2H).

Workup

  1. custom1-Benzyl-7-(3-chloro-4-fluorophenyl)-1H-indole was prepared
  2. customPurification by HPLC

Sources & evidence

ORD record
ord-a7ecc296cf1241b38026374809e6470c
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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