Pyridine → HCID 13442948, compound

HRID 2175347Notes

Reaction equation

HRID 2175347 reaction equation
O/[N:2]=[CH:3]/[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]([O:15][CH3:16])=[O:14].N1C=CC=CC=1.CS(Cl)(=O)=O>O1CCOCC1.O>[C:3]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]([O:15][CH3:16])=[O:14])#[N:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 135777574METHYL 3-[(HYDROXYIMINO)METHYL]-1H-INDOLE-2-CARBOXYLATE

Product 1

HCID 13442948HCID 13442948, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl 3-[(E)-(hydroxyimino)methyl]-1H-indole-2-carboxylate (from Key Organics, 1.0 g, 4.6 mmol) and pyridine (7.4 mL, 92 mmol) in 1,4-dioxane (20 mL) was added methanesulfonyl chloride (1.4 mL, 18 mmol). The reaction was heated at 60° C. for 2 hours. The reaction was diluted with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-5% MeOH/dichloromethane) to give the desired product (0.7 g, 76%). LCMS calculated for C11H9N2O2(M+H)+: m/z=201.1. Found: 201.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0-5% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-b9c5263f6d1b4ebbab71764942f3dbc7
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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