Iodobenzene → HCID 66765346, compound

HRID 1466797Notes

Reaction equation

HRID 1466797 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.N[C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1N.IC1C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12]=2[CH3:21])[CH:5]=1

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 66765016HCID 66765016, compound

Product 1

HCID 66765346HCID 66765346, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.252 g, 0.759 mmol), (±)-trans-1,2-diaminocyclohexane (18 μL, 0.15 mmol), iodobenzene (103 μL, 0.911 mmol), K3PO4 (0.402 g, 1.89 mmol) and copper(I) iodide (0.0072 g, 0.04 mmol) were dissolved in toluene (0.750 mL) and the reaction vessel was purged with N2 (g) for 1 minute. The reaction was heated to 120° C. and stirred overnight. Standard workup procedure followed by silica gel chromatography (0-20% EtOAc in hexanes) afforded the title compound.

Workup

  1. customthe reaction vessel was purged with N2 (g) for 1 minute

Sources & evidence

ORD record
ord-cbec38a856c0494c941def3babb35f1e
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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