Lithium Chloride → HCID 18789318, compound

HRID 1106621Notes

Reaction equation

HRID 1106621 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:11]([NH:13][C:14]1[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[NH:16][N:15]=1)=[O:12])[CH2:5]2.C([Sn](CCCC)(CCCC)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl-].[Li+]>CN1CCCC1=O>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[NH:16][N:15]=[C:14]([NH:13][C:11]([CH:6]3[CH2:5][C:4]4[C:8](=[CH:9][CH:10]=[C:2]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:3]=4)[CH2:7]3)=[O:12])[CH:18]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 607632TributylphenyltinHCID 18789300HCID 18789300, compound

Product 1

HCID 18789318HCID 18789318, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

3-(5-Bromoindan-2-yl)carbonylamino-5-(4-methoxyphenyl)pyrazole (50 mg), tributylphenyltin (0.12 ml), a tris(dibenzylideneacetone)dipalladium chloroform complex (6 mg), tri-2-furylphosphine (11 mg) and lithium chloride (25 mg) were dissolved in N-methylpyrrolidone (1 ml) with heating, and the mixture was heated at 85° C. overnight. After allowing to cool, the reaction solution was concentrated under a reduced pressure. The residue was dissolved in ethyl acetate-hexane (1:1, 30 ml) and the solution was washed with saturated aqueous potassium fluoride solution and dried over anhydrous magnesium sulfate. The solvent was distilled away under a reduced pressure. The resultant residue was purified by preparative thin layer chromatography (chloroform: methanol=20:1) to obtain the title compound (4.4 mg).

Workup

  1. temperaturewith heating
  2. temperatureto cool
  3. concentrationthe reaction solution was concentrated under a reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate-hexane (1:1, 30 ml)
  5. washthe solution was washed with saturated aqueous potassium fluoride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away under a reduced pressure
  8. customThe resultant residue was purified by preparative thin layer chromatography (chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-e48f2a3fbfff4d2eaeec5b0dbfceee51
Source dataset
uspto-grants-2000_05
Patent number
US06057335

Reaction notes

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