Lithium Chloride → HCID 21263001, compound

HRID 567795Notes

Reaction equation

HRID 567795 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14](=[O:26])[CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH:9]=2)[CH:5]=[N:6][CH:7]=1.[CH2:27](C([Sn])=C(CCCC)CCCC)[CH2:28]CC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl-].[Li+].[F-].[K+]>CN1CCCC1=O.C(Cl)(Cl)Cl>[CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[CH2:15][C:14]([NH:13][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([CH:27]=[CH2:28])[CH:3]=2)[NH:12][N:11]=1)=[O:26]

Participants

8

Reactant 5

HCID 433294Lithium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 522689Potassium FluorideHCID 21262994HCID 21262994, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 21263001HCID 21263001, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

5-(5-Bromo-3-pyridyl)-3-(2-naphthylacetyl)aminopyrazole (509.8 mg), tributylvinyl tin (1.1 ml), a tris(dibenzylideneacetone)dipalladium—chloroform complex (74.2 mg), tri-2-furylphosphine (133.3 mg) and lithium chloride (311.3 mg) were dissolved in N-methylpyrrolidone (10 ml) with heating, and the mixture was stirred at 80° C. overnight. After the reaction solution was allowed to cool, it was poured into a saturated aqueous potassium fluoride solution (100 ml)—chloroform (100 ml) and vigrously stirred for 30 minutes. The mixture was filtered through Celite and the filtrate was separated. The aqueous layer was extracted with chloroform (50 ml×3). The organic layers were combined, dried over anhydrous magnesium sulfate and treated with an activated carbon. Then, the solvent was distilled away under a reduced pressure. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=5: 1→chloroform:methanol=10:1) and then crystallized from chloroform to obtain the title compound (58.8 mg) as white crystals (melting point: 218-220° C.).

Workup

  1. temperaturewith heating
  2. temperatureto cool
  3. stirringvigrously stirred for 30 minutes
  4. filtrationThe mixture was filtered through Celite
  5. customthe filtrate was separated
  6. extractionThe aqueous layer was extracted with chloroform (50 ml×3)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. additiontreated with an activated carbon
  9. distillationThen, the solvent was distilled away under a reduced pressure
  10. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=5: 1→chloroform:methanol=10:1)
  11. customcrystallized from chloroform

Sources & evidence

ORD record
ord-48cc9b10e19940c3bdc1499d4504d2e1
Source dataset
uspto-grants-2001_01
Patent number
US06180653B2

Reaction notes

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