Indole → HCID 21940715, compound

HRID 1883418Notes

Reaction equation

HRID 1883418 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:11]1[CH:16]=CC=C[N:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1NC>[Cu]I.CCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:27]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH2:16][CH2:11][NH2:12])=[CH:2]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 798IndoleHCID 79772-ChloropyridineHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 21940715HCID 21940715, compoundYield 410.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the general procedure, indole (0.117 g, 1.00 mmol) was coupled with 2-chloropyridine (113 μL, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (32 μL, 0.20 mmol, 20 mol %) and toluene (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 9:1) provided 0.194 g (100% yield) of the product as a yellow oil. 1H NMR (400 MHz, CDCl3): δ9.24 (s, 1H), 9.05 (s, 1H), 8.41 (s, 1H), 7.75 (m, 2H), 7.60 (m, 2H), 7.48 (m, 1H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-9b7d3c6990f847d6841038515984a695
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

Loading…