Lithium Chloride → HCID 18789323, compound

HRID 1106616Notes

Reaction equation

HRID 1106616 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14]([CH:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.[CH2:25](C([Sn])=C(CCCC)CCCC)[CH2:26]CC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl-].[Li+]>CN1CCCC1=O.C(OCC)(=O)C.CCCCCC>[CH2:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][CH:16]1[C:14]([NH:13][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:25]=[CH2:26])=[CH:3][CH:4]=2)[NH:12][N:11]=1)=[O:15]

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 18789311HCID 18789311, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 18789323HCID 18789323, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

5-(4-Bromophenyl)-3-(2-indanyl)carbonylaminopyrazole (106.5 mg), tributylvinyltin (0.25 ml), a tris(dibenzylideneacetone)dipalladium chloroform complex (17.1 mg), tri-2-furylphosphine (34.4 mg) and lithium chloride (34.0 mg) were dissolved in N-methylpyrrolidone (2 ml) with heating, and the resultant mixture was heated at 80° C. overnight. After allowing to cool, the reaction solution was diluted with ethyl acetate-hexane (1:1, 100 ml), washed with saturated aqueous potassium fluoride solution (100 ml×2) and then dried over anhydrous magnesium sulfate. The solvent was distilled away under a reduced pressure. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) and then crystallized from chloroform to obtain the title compound (70.2 mg) as white crystals (melting point: 193-195° C.).

Workup

  1. temperaturewith heating
  2. temperatureto cool
  3. washwashed with saturated aqueous potassium fluoride solution (100 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away under a reduced pressure
  6. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)
  7. customcrystallized from chloroform

Sources & evidence

ORD record
ord-d41a0a12af6f4a5389a496901cd47345
Source dataset
uspto-grants-2000_05
Patent number
US06057335

Reaction notes

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