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

HRID 591406Notes

Reaction equation

HRID 591406 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([Cl:15])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.[CH3:17][C:18]1[C:23]([CH2:24]O)=[CH:22][CH:21]=[C:20]([C:26]([F:29])([F:28])[F:27])[N:19]=1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([Cl:15])=[CH:11][C:12]([O:14][CH2:24][C:23]3[C:18]([CH3:17])=[N:19][C:20]([C:26]([F:29])([F:27])[F:28])=[CH:21][CH:22]=3)=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolHCID 20770824Methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetate

Product 1

HCID 71721632Methyl(4-chloro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetate (110 mg) and THF (dry) (5 mL) were added (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (82 mg), tri-n-butylphosphine (0.159 mL), and ADDP (130 mg) at room temperature. The mixture was stirred at room temperature for 12 h. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (164 mg). The compound was crystallized from IPE-hexane.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-c692b59b4e41434f8b4cde10088f6389
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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