Bromobenzene → HCID 29923744, compound

HRID 624664Notes

Reaction equation

HRID 624664 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN[C@@H]1CCCC[C@H]1NC>[Al].[Cu]I.C1(C)C=CC=CC=1>[C:23]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 7961BromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 589098Methyl indole-3-carboxylateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 29923744HCID 29923744, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 5359268AluminumSolvent

Conditions

Temperature
110 °C

Procedure

A 5 mL screwtop vial containing methyl 1H-indole-3-carboxylate (100 mg, 0.571 mmol) and potassium phosphate (254 mg, 1.199 mmol) was degassed and purged with nitrogen after the addition of each of the following in sequential order: PhMe (1142 μl), bromobenzene (59.7 μl, 0.571 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (54.4 μl, 0.342 mmol), and copper(I) iodide (32.6 mg, 0.171 mmol). The vial was sealed, wrapped in aluminum foil, and heated to 110° C. for 24 h. Concentration on silica gel and ISCO purification (20% EtOAc/hexanes) gave the title compound as a white solid.

Workup

  1. customwas degassed
  2. custompurged with nitrogen
  3. additionafter the addition of each of the following in sequential order
  4. customThe vial was sealed
  5. concentrationConcentration
  6. customon silica gel and ISCO purification (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dc40fdff76254aee8f27df88bdf28093
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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