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

HRID 591461Notes

Reaction equation

HRID 591461 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: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]([Cl: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 121006517Methyl 2-(4-chloro-7-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate

Product 1

HCID 118667010Methyl(4-chloro-7-fluoro-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (0.264 mL), methyl(4-chloro-7-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate (116 mg), (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (89 mg) and THF (4.0 mL) was added ADDP (213 mg) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere for 1 h. The mixture was concentrated in vacuo. 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 (172 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  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-086d3c0f17774deeaa9d901c6bc01225
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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