Tributylphosphine → HCID 67528557, compound

HRID 2261857Notes

Reaction equation

HRID 2261857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22](O)[CH3:23])=[C:18]([CH3:25])[CH:17]=2)=[C:12]([CH:26]([CH3:28])[CH3:27])[CH:11]=[N:10]1.[CH3:29][O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([SH:38])[CH:33]=1.CCCCP(CCCC)CCCC>C1(C)C=CC=CC=1>[CH3:29][O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([S:38][CH:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:13]3[N:9]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[N:10]=[CH:11][C:12]=3[CH:26]([CH3:27])[CH3:28])=[CH:17][C:18]=2[CH3:25])[CH3:23])[CH:33]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 4362804Methyl 3-mercaptobenzoateHCID 675280881-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-ethanol

Product 1

HCID 67528557HCID 67528557, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To an ambient temperature solution of 1-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-ethanol (75 mg, 1.78 mmol) in toluene (20 mL) are added 3-Mercapto-benzoic acid methyl ester (299 mg, 1.78 mmol) and tri-N-butylphosphine (668 μL, 2.68 mmol). The reaction mixture is cooled to 0° C. 1,1′-(Azocarbonyl)-dipiperidine (676 mg, 2.68 mmol) is added and the reaction mixture is warmed to room temperature overnight. The reaction mixture is concentrated and the residue is chromatographed (40 g SiO2, 0% to 30% EtOAc/Hexanes) to yield the title compound (541 mg, 54%). 1H NMR (400 MHz, CDCl3) δ 8.00-7.98 (m, 1H), 7.99 (t, 1H, J=1.8 Hz), 7.87 (dt, 1H, J=4.6, 2.5 Hz), 7.70 (s, 1H), 7.43-7.39 (m, 3H), 7.32-7.22 (m, 3H), 6.61-6.54 (m, 2H), 4.79 (s, 2H), 4.53 (q, 1H, J=7.0 Hz), 3.90 (s, 3H), 2.99 (sept, 1H, J=6.6 Hz), 2.32 (s, 3H), 1.56 (d, 3H, J=6.9 Hz), 1.30 (d, 6H, J=6.6 Hz).

Workup

  1. temperaturethe reaction mixture is warmed to room temperature overnight
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue is chromatographed (40 g SiO2, 0% to 30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e18018832c2848fdb6e78f49d35668d6
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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