Tributylphosphine → 1-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-ethanone

HRID 2261751Notes

Reaction equation

HRID 2261751 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[C:24]([CH2:25]O)=[C:23]([CH:27]([CH3:29])[CH3:28])[CH:22]=[N:21]1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[C:24]([CH2:25][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=2)=[C:23]([CH:27]([CH3:29])[CH3:28])[CH:22]=[N:21]1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 701334-Hydroxy-2-methylacetophenoneHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

Product 1

HCID 574432701-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 0° C. suspension of 4′-Hydroxy-2′-methylacetophenone (716 mg, 4.77 mmol), [2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-methanol (1.36 g, 4.77 mmol), tri-n-butylphosphine (1.78 mL, 7.15 mmol) in toluene (20 mL) is added ADDP (1.80 g, 7.15 mmol). The reaction is warmed to room temperature and is stirred overnight. The reaction is concentrated under reduced pressure and the residue is chromatographed (0% to 30% EtOAc/Hex) to yield the title compound (857 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 7.65 (d, 1H, J=8.8 Hz), 7.42-7.38 (m, 2H), 7.32-7.27 (m, 1H), 6.64-6.58 (m, 2H), 4.85 (s, 2H), 2.99 (sept, 1H, J=7.0 Hz), 2.50 (s, 3H), 2.49 (s, 3H), 1.30 (d, 6H, J=7.0 Hz).

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. customthe residue is chromatographed (0% to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-4c1aaefa286847ff8d685d77719baf90
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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