Tributylphosphine → HCID 57652739, compound

HRID 424851Notes

Reaction equation

HRID 424851 reaction equation
[CH:1]1([C:4]2[N:8]=[N:7][N:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17][OH:18])[CH2:3][CH2:2]1.[CH3:19][O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:37]=[CH:36][C:35](O)=[CH:34][C:33]=3[CH3:39])=[CH:29][CH:30]=2)[N:25]([CH:40]([CH3:42])[CH3:41])[N:24]=1)=[O:22].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:37]=[CH:36][C:35]([O:18][CH2:17][C:5]4[N:6]([C:9]5[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=5[Cl:16])[N:7]=[N:8][C:4]=4[CH:1]4[CH2:3][CH2:2]4)=[CH:34][C:33]=3[CH3:39])=[CH:29][CH:30]=2)[N:25]([CH:40]([CH3:42])[CH3:41])[N:24]=1)=[O:22]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 66704182HCID 66704182, compoundHCID 136342877HCID 136342877, compound

Product 1

HCID 57652739HCID 57652739, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Nitrogen is bubbled through a solution of [5-cyclopropyl-3-(2,6-dichloro-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol (0.23 g, 0.80 mmol) and 6-(4-hydroxy-2-methyl-phenyl)-1-isopropyl-1H-indazole-3-carboxylic acid methyl ester (0.2 g, 0.62 mmol) in toluene (10 mL) for 10 minutes. Tri-n-butyl phosphine (0.21 mL, 1.05 mmol) is added. Nitrogen is bubbled for an additional 10 min followed by addition of 1,1′-(azocarbonyl)-dipiperidine (0.27 g, 1.05 mmol). The reaction is stirred at room temperature for 18 h. The crude reaction is concentrated onto silica and chromatographed (40 g SiO2, 0% to 40% EtOAc/Hexanes) to yield the title compound (0.11 g, 30%). LC-ES/MS m/e 590.0 (M+1).

Workup

  1. customNitrogen is bubbled for an additional 10 min
  2. customThe crude reaction
  3. concentrationis concentrated onto silica
  4. customchromatographed (40 g SiO2, 0% to 40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-d34d72beec974030b63c88c222a6e85b
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

Loading…