Potassium Phosphate, Tribasic → HCID 11601742, compound

HRID 252483Notes

Reaction equation

HRID 252483 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC.[O:28]1[C:32]2=[CH:33][C:34]3[C:35]([C:40]#[N:41])=[CH:36][NH:37][C:38]=3[CH:39]=[C:31]2[O:30][CH2:29]1>C1(C)C=CC=CC=1.[Cu]I>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:37]2[C:38]3[CH:39]=[C:31]4[O:30][CH2:29][O:28][C:32]4=[CH:33][C:34]=3[C:35]([C:40]#[N:41])=[CH:36]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 696764-IodoanisoleHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 59425696HCID 59425696, compound

Product 1

HCID 11601742HCID 11601742, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of p-iodoanisole (85 mg, 0.36 mmol), anhydrous K3PO4 (102 mg, 0.48 mmol), CuI (4.6 mg, 0.024 mmol) and N,N′-Dimethyl cyclohexane-1,2-diamine (14 mg, 0.096 mmol) is added to 5H-[1,3]dioxolo[4,5-f]indole-7-carbonitrile (45 mg, 0.24 mmol), prepared as described by the method of example 1A, step A, in anhydrous toluene (0.4 mL). After heating at reflux for 24 h, the solvent is evaporated under vacuum. The residue is dissolved with CH2Cl2 (5 mL) and the mixture is filtered. The filtrate is concentrated to afford crude product, which is purified by silica gel chromatography using EtOAc/petroleum ether (1:4) as eluent to yield 5-(4-methoxyphenyl)-5H-[1,3]dioxolo[4,5-f]indole-7-carbonitrile.

Workup

  1. customprepared
  2. temperatureAfter heating
  3. temperatureat reflux for 24 h
  4. customthe solvent is evaporated under vacuum
  5. dissolutionThe residue is dissolved with CH2Cl2 (5 mL)
  6. filtrationthe mixture is filtered
  7. concentrationThe filtrate is concentrated
  8. customto afford crude product, which
  9. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-49c1f6f5c6bf4168b61d5166f162fef0
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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