Tributylphosphine → Methyl(4-chloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

HRID 591416Notes

Reaction equation

HRID 591416 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][N:18]1[C:22]([CH2:23]O)=[CH:21][C:20]([C:25]([F:28])([F:27])[F:26])=[N:19]1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C(P(CCCC)CCCC)CCC>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][CH2:23][C:22]3[N:18]([CH3:17])[N:19]=[C:20]([C:25]([F:28])([F:26])[F:27])[CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 20770824Methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetateHCID 58456726(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol

Product 1

HCID 89768906Methyl(4-chloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(4-chloro-6-hydroxy-1-benzothiophen-3-yl)acetate (750 mg) and THF (dry) (10 mL) were added (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (632 mg), ADDP (958 mg) and tri-n-butylphosphine (1.442 mL) at room temperature. The mixture was stirred at room temperature for 16 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). The product was crystallized from EtOAc-hexane to give the title compound (1132 mg).

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)
  4. customThe product was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-041391583e3643589598e1b4bcc8696f
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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