Triethylamine → HCID 57882762, compound

HRID 1817767Notes

Reaction equation

HRID 1817767 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[N:11]([C@H:22]([C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)[CH3:23])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[CH:43]=[C:42](B(O)O)[CH:41]=[CH:40]2.C(N(CC)CC)C>C(COC)OC>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:13]=[C:12]([C:42]3[CH:41]=[CH:40][C:39]4[C:44](=[CH:45][CH:46]=[C:37]([O:36][CH3:35])[CH:38]=4)[CH:43]=3)[N:11]([C@H:22]([C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)[CH3:23])[N:10]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46416926-Methoxy-2-naphthaleneboronic acidHCID 71650815Benzoic acid, 4-[(1S)-1-[3-(3,5-dichlorophenyl)-5-[[(trifluoromethyl)sulfonyl]oxy]-1H-pyrazol-1-yl]ethyl]-, ethyl ester

Product 1

HCID 57882762HCID 57882762, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-[(1S)-1-(3-(3,5-dichlorophenyl)-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazol-1-yl)ethyl]benzoate (2.15 g, 4.0 mmol), 6-methoxy-2-naphthylboronic acid (1.18 g, 6.0 mmol) and triethylamine (1.2 ml, 8.0 mmol) were dissolved in dimethoxyethane (40 ml) in a thick-wall tube. The reaction mixture was purged with N2 for 15 min. Catalyst Pd(PPh3)4 (350 mg, 8%) was added, and the test tube was heated in a microwave reactor to 100° C. for 15 min. The solvent was removed under reduced pressure, and the residue partitioned between ethyl acetate and IN HCl. The organic layer was washed with 0.5 NH4Cl 2×, brine 2×, dried over Na2SO4, and filtered through a Celite pad. The crude product was purified by column chromatography (SiO2, 10-15% ethyl acetate in hexanes) to give ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxy-2-naphthyl)-1H-pyrazol-1-yl]ethyl}benzoate as a dry film. NMR (500 MHz, CDCl3) δ: 1.38 (t, J=7.1 Hz, 3H); 1.96 (d, J=7.0 Hz, 3H); 3.95 (s, 3H; 4.37 (q, J=7.1 Hz, 2H); 5.59 (q, J=7.0 Hz, 1H); 6.65 (s, 1H); 7.17 (d, J=2.6 Hz, 1H); 7.20 (dd, J=2.6, 8.9 Hz, 1H); 7.28 (d, J=8.4 Hz, 2H); 7.29 (dd, J=1.8, 8.5 Hz, 1H); 7.30 (t, J=1.9 Hz, 1H); 7.63 (d, J=1.8 Hz, 1H); 7.67 (d, J=8.9 Hz, 1H); 7.76 (d, J=8.5 Hz, 1H); 7.80 (d, J=1.9 Hz, 2H); 7.99 (d, J=8.4 Hz, 2H); MS C31H26Cl2N2O3 Cald: 544.13; Obsd: 545.15.

Workup

  1. customThe reaction mixture was purged with N2 for 15 min
  2. additionCatalyst Pd(PPh3)4 (350 mg, 8%) was added
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate and IN HCl
  5. washThe organic layer was washed with 0.5 NH4Cl 2×, brine 2×
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through a Celite pad
  8. customThe crude product was purified by column chromatography (SiO2, 10-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e79848485bee4aeeb6027051bb722a60
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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