Chlorosuccinimide → Ethyl 7-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine-7-carboxylate

HRID 71213Notes

Reaction equation

HRID 71213 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[N:17][N:18]3[CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:22][CH2:21][CH2:20][C:19]=23)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl:39]N1C(=O)CCC1=O>C1COCC1.C(OCC)(=O)C>[Cl:39][C:23]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:18]2[N:17]=[N:16][C:15]([C:5]3[CH:6]=[CH:7][C:8]([C:9]4[O:13][C:12]([CH3:14])=[N:11][CH:10]=4)=[C:3]([O:2][CH3:1])[CH:4]=3)=[C:19]2[CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 2733832Lithium HexamethyldisilazideHCID 66608315Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine-7-carboxylate

Product 1

HCID 66608316Ethyl 7-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine-7-carboxylateYield 128.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine-7-carboxylate (1.00 g) in THF (52 mL) was added lithiumhexamethyl disilazide (1M THF solution, 3.14 mL) at −78° C. under an argon atmosphere. The reaction mixture was stirred at −78° C. for 20 min, and at 0° C. for 20 min. To the reaction mixture was added N-chlorosuccinimide (419 mg) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.40 g).

Workup

  1. waitat 0° C. for 20 min
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c84a528aae9f430dbdba8d2171695abd
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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