Tributylphosphine → Methyl(7-fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591450Notes

Reaction equation

HRID 591450 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]([CH3:29])=[CH:24][C:25]([OH:28])=[C:26]([F:27])[C:21]=2[S:20][CH:19]=1.[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]([CH3:29])=[CH:24][C:25]([O:28][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)=[C:26]([F:27])[C:21]=2[S:20][CH:19]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolHCID 121003808Methyl(7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 89775297Methyl(7-fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (0.362 mL), methyl(7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (122.8 mg), (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (102 mg) and THF (4.5 mL) was added ADDP (305 mg) at room temperature. The mixture was stirred overnight at room temperature under nitrogen atmosphere. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, EtOAc/hexane) to give the title compound (196 mg). The compound 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 (NH, EtOAc/hexane)

Sources & evidence

ORD record
ord-b8b7bbe26cf84bfdab1c4cd6ad01e9dd
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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