4-Bromotoluene → HCID 11311072, compound

HRID 1883420Notes

Reaction equation

HRID 1883420 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([Cl:1])=[N:3]2)=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 78054-BromotolueneHCID 62657Potassium Phosphate, TribasicHCID 958943-Chloro-1H-indazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 11311072HCID 11311072, compoundYield 87%

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, 3-chloroindazole (0.153 g, 1.00 mmol) was coupled with 4-bromotoluene, (148 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 50:1) provided 0.211 g (87% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ7.70 (d, J=8.2 Hz, 1H), 7.63 (d, J=8.5 Hz, 1H), 7.52 (m, 2H), 7.43 (m, 1H), 7.24 (d, J=8.2 Hz, 2H),7.22 (m, 1H), 2.38 (s, 3H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-6017f2d0198d457eb247161f2614ee2d
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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