Potassium Phosphate, Tribasic → HCID 11601742, compound

HRID 907091Notes

Reaction equation

HRID 907091 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) was 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 was evaporated under vacuum. The residue was dissolved with CH2Cl2 (5 mL) and the mixture was filtered. The filtrate was concentrated to afford crude product, which was 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 was evaporated under vacuum
  5. dissolutionThe residue was dissolved with CH2Cl2 (5 mL)
  6. filtrationthe mixture was filtered
  7. concentrationThe filtrate was concentrated
  8. customto afford crude product, which
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-df12b596c15843648be7496696bf569a
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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