HCID 69813110, compound → HCID 86651535, compound

HRID 1809453Notes

Reaction equation

HRID 1809453 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[N:12]3[C:21]=2/[CH:22]=[CH:23]/[O:24]CC)=[CH:5][CH:4]=1)#[N:2]>C1COCC1.O.[Hg](OC(C)=O)OC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[N:12]3[C:21]=2[CH2:22][CH:23]=[O:24])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 69813110HCID 69813110, compound

Product 1

HCID 86651535HCID 86651535, compound

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A stirred solution of (A4) in a mixture of THF/H2O 9:1 (0.2 M) was treated with Hg(OAc)2 (1.5 eq.). After the reaction mixture was stirred at 50° C. for 3 h, freshly prepared sat. aq. KI was added and stirring was continued at RT for 10 min. Then, the reaction mixture was extracted with EtOAc, washed with sat. aq. Na2S2O4 and dried (Na2SO4). Evaporation of the solvent gave methyl 2-(4-cyanophenyl)-3-(2-oxoethyl)imidazo[1,2-a]pyridine-5-carboxylate which was used in the next step without further purification. MS (ES+) C18H13N3O3 requires: 319, found: 320 (M+H)+.

Workup

  1. additionfreshly prepared sat. aq. KI was added
  2. stirringstirring
  3. waitwas continued at RT for 10 min
  4. extractionThen, the reaction mixture was extracted with EtOAc
  5. washwashed with sat. aq. Na2S2O4
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-314229d71b344ea1a8bd493e6e3924f6
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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