Potassium Carbonate → HCID 66673097, compound

HRID 423676Notes

Reaction equation

CS([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[O:17][N:16]=[C:15]([CH:18]([CH3:20])[CH3:19])[N:14]=2)[CH2:9][CH2:8]1)(=O)=O.Cl.[F:22][C:23]1[CH:28]=[C:27]([S:29][CH3:30])[CH:26]=[CH:25][C:24]=1[C:31]1[N:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:22][C:23]1[CH:28]=[C:27]([S:29][CH3:30])[CH:26]=[CH:25][C:24]=1[C:31]1[CH:32]=[CH:33][C:34]([O:5][CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[O:17][N:16]=[C:15]([CH:18]([CH3:19])[CH3:20])[N:14]=3)[CH2:11][CH2:12]2)=[CH:35][N:36]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl methanesulfonate (prepared as in Example 100, Step 4, 50.4 g, 166 mmol), 6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinol hydrochloride (47.6 g, 175 mmol), powdered potassium carbonate (72.6 g, 525 mmol) and N,N-dimethylformamide (450 mL) was mechanically stirred and heated at 80° C. under nitrogen for 48 h. The reaction was cooled to ambient temperature, poured onto ice water (2.5 L) and allowed to stand for 30 min. The resulting solid was filtered, rinsed with water (500 mL), heptane (500 mL) and air-dried to afford 2-[2-fluoro-4-(methylthio)phenyl]-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyridine (67.5 g, 92%) as a light tan solid.

Workup

temperatureThe reaction was cooled to ambient temperature
additionpoured onto ice water (2.5 L)
filtrationThe resulting solid was filtered
washrinsed with water (500 mL), heptane (500 mL)
customair-dried

Sources & evidence

ORD record: ord-1964b24581264e36ab97e44d89948117
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101634B2

Reaction notes

Loading…