HCID 68285193, compound → HCID 68285229, compound

HRID 1497667Notes

Reaction equation

HRID 1497667 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[S:13][C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.C(O)(=O)C.[Zn]>[N:18]1[CH:19]=[CH:20][C:15]([C:14]2[S:13][C:12]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:11][C:10]=2[C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[NH2:1])=[CH:16][CH:17]=1

Participants

5

Reactant 1

HCID 68285193HCID 68285193, compound

Product 1

HCID 68285229HCID 68285229, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 4-[4-(3-nitrophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]pyridine in absolute ethanol (5 mL) and acetic acid (1 mL), zinc (300 mg) was added. The mixture was stirred and heated to reflux for 3 h. The mixture was dried up and treated with a small amount of 1 N HCl. After stirring for 1 h, the solution was brought to pH 14 using sodium hydroxide and extracted with DCM. The organic layer was dried with sodium sulfate and evaporated to driness. The solid material so obtained was purified by silica gel column chromatography eluting with ethyl acetate/hex/ammonium hydroxyde 8/2/0.1 yielding the title compound (52 mg, 59%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customThe mixture was dried up
  4. additiontreated with a small amount of 1 N HCl
  5. stirringAfter stirring for 1 h
  6. extractionextracted with DCM
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. customevaporated to driness
  9. customThe solid material so obtained
  10. customwas purified by silica gel column chromatography
  11. washeluting with ethyl acetate/hex/ammonium hydroxyde 8/2/0.1 yielding the title compound (52 mg, 59%)

Sources & evidence

ORD record
ord-cc5ac703a55f43e2a5dc30cff444c9de
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

Loading…