Cesium carbonate → Ethyl 1-(6-(2-((4-bromobenzyl)oxy)-5-methylphenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1891222Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[N:16]2)[CH:12]=[CH:11][CH:10]=1.[Br:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=2[C:9]2[N:14]=[C:13]([N:15]3[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[N:16]3)[CH:12]=[CH:11][CH:10]=2)=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a vial containing the title compound from Example 12 Step B (320 mg, 0.82 mmol) were added 4-bromobenzyl bromide (245 mg, 0.98 mmol), cesium carbonate (533 mg, 1.64 mmol), and DMF (3 mL), and the resulting mixture was stirred at 45° C. After 1 h, the reaction mixture was allowed to cool to ambient temperature, then was loaded directly onto a silica gel column and purified (0 to 30% EtOAc in hexanes, then 30% EtOAc in hexanes) to provide the title compound: LCMS m/z 562.4 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.77 (d, J=3.0 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.22 (d, J=8.5 Hz, 2H), 7.16 (dd, J=8.0, 3.0 Hz, 1H), 6.92 (d, J=8.5 Hz, 1H), 5.06 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 2.35 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).

Workup

temperatureto cool to ambient temperature
custompurified (0 to 30% EtOAc in hexanes

Sources & evidence

ORD record: ord-4450654c96a94923a569a989f255cf29
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507512B2

Reaction notes

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