Sodium hydride → 5-(4-(6-Bromobenzo[d]thiazol-2-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1429566Notes

Reaction equation

[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[Br:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24](Cl)[S:25][C:21]=2[CH:20]=1>C1COCC1.O>[Br:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24]([O:15][CH:12]3[CH2:11][CH2:10][N:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:14][CH2:13]3)[S:25][C:21]=2[CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-ol (590 mg, 2.79 mmol) in THF (20 mL) was added NaH (60% in mineral oil, 142 mg, 3.55 mmol) followed by 6-bromo-2-chlorobenzo[d]thiazole (631 mg, 2.54 mmol). The reaction mixture was stirred at 60° C. for 4 h. The mixture was cooled to rt, diluted with water (40 mL), and extracted with EtOAc (3×30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 50% EtOAc) to afford 5-(4-(6-bromobenzo[d]thiazol-2-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole (697 mg, 1.646 mmol, 65% yield) as a white solid.

Workup

temperatureThe mixture was cooled to rt
extractionextracted with EtOAc (3×30 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 50% EtOAc)

Sources & evidence

ORD record: ord-b5fff78ef33a4cbbac77b9b0346f8d7e
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940716B2

Reaction notes

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