Tributylphosphine → HCID 118667068, compound

HRID 591572Notes

Reaction equation

HRID 591572 reaction equation
C(P(CCCC)CCCC)CCC.[CH3:14][O:15][C:16](=[O:30])[CH2:17][C:18]1[C:22]2[C:23]([Cl:28])=[CH:24][C:25]([OH:27])=[CH:26][C:21]=2[S:20][C:19]=1[CH3:29].[CH3:31][C:32]1[C:37]([CH2:38]O)=[CH:36][CH:35]=[C:34]([C:40]([F:43])([F:42])[F:41])[N:33]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:14][O:15][C:16](=[O:30])[CH2:17][C:18]1[C:22]2[C:23]([Cl:28])=[CH:24][C:25]([O:27][CH2:38][C:37]3[C:32]([CH3:31])=[N:33][C:34]([C:40]([F:43])([F:41])[F:42])=[CH:35][CH:36]=3)=[CH:26][C:21]=2[S:20][C:19]=1[CH3:29]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolHCID 131734536HCID 131734536, compound

Product 1

HCID 118667068HCID 118667068, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (0.418 mL), methyl(4-chloro-6-hydroxy-2-methyl-1-benzothiophen-3-yl)acetate (151.2 mg) and (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (112 mg) and THF (5.0 mL) was added ADDP (423 mg) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere for 1 h. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (165 mg). The solid was crystallized from EtOAc-hexane.

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added IPE
  3. filtrationthe precipitate was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-1e738883315041b88013efca891d1d98
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

Loading…