Tert-butyl 2-diazoacetate → HCID 67359527, compound

HRID 1185996Notes

Reaction equation

HRID 1185996 reaction equation
[N+](=[CH:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[N-].[CH3:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:18]=[C:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)[N:20]=2)[CH:17]=1>C1(C)C=CC=CC=1.[Cu]>[C:7]([O:6][C:4]([CH2:3][C:18]1[N:16]2[CH:17]=[C:12]([CH3:11])[CH:13]=[CH:14][C:15]2=[N:20][C:19]=1[C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1)=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 5097903Tert-butyl 2-diazoacetateHCID 67359044HCID 67359044, compound

Product 1

HCID 67359527HCID 67359527, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

Tert-butyl diazoacetate (5 ml, 35.15 mmol) then copper powder (2.5 g) were gradually added to a refluxing solution of 9 (5.0 g, 18.8 mmol) in anhydrous toluene (150 ml). After a further 3 h of reflux, the mixture was cooled to room temperature, the suspension filtered and dried. Purification by column chromatography on silica gel (ethyl acetate-hexane, 1:1) gave methyl 4-(3-tert-butoxycarbonylmethyl-6-methylimidazo[1,2-a]pyridin-2-yl)benzoate 10 (3.35 g, 47%).

Workup

  1. temperatureAfter a further 3 h of reflux
  2. filtrationthe suspension filtered
  3. customdried
  4. customPurification by column chromatography on silica gel (ethyl acetate-hexane, 1:1)

Sources & evidence

ORD record
ord-d408cbcbcf654e44bda08bbaf5d39240
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

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