Potassium Phosphate, Tribasic → HCID 59627929, compound

HRID 2421225Notes

Reaction equation

HRID 2421225 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:21]([F:33])[CH:20]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@H]1CCCC[C@@H]1NC>C1(C)C=CC=CC=1.[Cu]I>[F:33][C:21]1[CH:20]=[C:19]([N:13]2[C:14]3[C:10](=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 884654-(phenylmethoxy)-1H-indoleHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzene

Product 1

HCID 59627929HCID 59627929, compoundYield 36.5%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-benzyloxyindole (3.35 g, 15 mmol), 4-bromo-2-fluoro-1-[(phenylmethyl)oxy]benzene (4.22 g, 15 mmol) and potassium phosphate (6.68 g, 31.5 mmol) in toluene (25 mL) was degassed by bubbling argon through the solution for 3 minutes. Copper (I) iodide (143 mg, 0.75 mmol) and (1S,2S)-N,N′-dimethyl-1,2-cyclohexanediamine (426 mg, 0.479 ml, 3.0 mmol) were added and the mixture was refluxed under argon for 24 hrs. After cooling, the mixture was filtered through a plug of silica gel (elution with ethyl acetate) and concentrated. Chromatography (2 columns, elution with 0-50% ethyl acetate in hexane and then a gradient of diethyl ether in hexane) gave the title compound (D1) 2.32 g.

Workup

  1. customwas degassed
  2. customby bubbling argon through the solution for 3 minutes
  3. temperaturethe mixture was refluxed under argon for 24 hrs
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through a plug of silica gel (elution with ethyl acetate)
  6. concentrationconcentrated
  7. washChromatography (2 columns, elution with 0-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ca160bb5e1ef4133b720c7456ea94d59
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

Loading…