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

HRID 591400Notes

Reaction equation

HRID 591400 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.[CH3:26][O:27][C:28](=[O:41])[CH2:29][C:30]1[C:34]2[C:35]([CH3:40])=[CH:36][C:37](O)=[CH:38][C:33]=2[S:32][CH:31]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:26][O:27][C:28](=[O:41])[CH2:29][C:30]1[C:34]2[C:35]([CH3:40])=[CH:36][C:37]([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:38][C:33]=2[S:32][CH:31]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58456726(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanolHCID 121001301Methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 89775282Methyl(4-methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetateYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tri-n-butylphosphine (0.162 mL), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (90 mg), methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (118 mg) and THF (5.0 mL) was added ADDP (164 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, the precipitate was filtered off, and 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 (148.4 mg).

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-298dcd1bc4964778aa0c5ff233838e44
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

Loading…