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

HRID 591408Notes

Reaction equation

HRID 591408 reaction equation
C(P(CCCC)CCCC)CCC.[CH3:14][N:15]1[C:19]([CH2:20][OH:21])=[CH:18][C:17]([C:22]([F:25])([F:24])[F:23])=[N:16]1.[CH2:26]([O:28][C:29](=[O:41])[CH2:30][C:31]1[C:35]2[CH:36]=[CH:37][C:38](O)=[CH:39][C:34]=2[S:33][CH:32]=1)[CH3:27].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH2:26]([O:28][C:29](=[O:41])[CH2:30][C:31]1[C:35]2[CH:36]=[CH:37][C:38]([O:21][CH2:20][C:19]3[N:15]([CH3:14])[N:16]=[C:17]([C:22]([F:23])([F:24])[F:25])[CH:18]=3)=[CH:39][C:34]=2[S:33][CH:32]=1)[CH3:27]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterHCID 58456726(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol

Product 1

HCID 89768891Ethyl(6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (0.165 mL), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (110 mg), ethyl(6-hydroxy-1-benzothiophen-3-yl)acetate (120 mg), and THF (5.0 mL) was added ADDP (167 mg) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere overnight. 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) and then silica gel column chromatography (EtOAc/hexane) to give the title compound (173 mg). The solid was crystallized from EtOH-hexane to give the title compound.

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-02844995eeb64b6e8f2291c10fb419da
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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