HCID 66926165, compound → HCID 66926115, compound

HRID 2170814Notes

Reaction equation

HRID 2170814 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH3:28])=[C:11]([CH:13]3[C:17](=[O:18])/[C:16](=[CH:19]/[C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)/[CH2:15][C:14]3=[O:27])[N:12]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH3:28])=[C:11]([CH:13]3[C:17](=[O:18])[CH:16]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)[CH2:15][C:14]3=[O:27])[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66926165HCID 66926165, compound

Product 1

HCID 66926115HCID 66926115, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(5-fluoro-pyridin-2-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione (70 mg, 0.17 mmol) in glacial acetic acid (2 ml) was added zinc powder (10 mg), and the reaction heated to 80° C. for 17 hours. The crude reaction mixture was then dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-(5-fluoro-pyridin-2-ylmethyl)-cyclopentane-1,3-dione (55 mg).

Workup

  1. customThe crude reaction mixture
  2. customwas then dry
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-0bf338e0dc5247f79c6e7259d3948204
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

Loading…