N-Iodosuccinimide → HCID 69077347, compound

HRID 1916623Notes

Reaction equation

HRID 1916623 reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[N:9]=[CH:8]1.[I:22]N1C(=O)CCC1=O>CCCCCC.C1COCC1>[I:22][C:8]1[N:7]([CH3:6])[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[N:9]=1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 67362954HCID 67362954, compoundHCID 178418339Butyllithium

Product 1

HCID 69077347HCID 69077347, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

0.80 mL (1.28 mmol) 1.6 M n-butyllithium solution in hexane are added to a solution, cooled to −75° C., of 250 mg (1.16 mmol) 1-methyl-5-pyrrolidin-1-ylmethyl-1H-benzimidazole in 8 mL THF. The reaction mixture is stirred for 10 min at this temperature and then 288 mg (1.28 mmol) N-iodosuccinimide in 5 mL THF are added. The cooling bath is removed and the reaction stirred for 1 h at RT. 12 mL 0.1 M HCl are added and the aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH/NH3 9:1:0.1).

Workup

  1. customThe cooling bath is removed
  2. stirringthe reaction stirred for 1 h at RT
  3. addition12 mL 0.1 M HCl are added
  4. extractionthe aqueous phase is extracted with EtOAc
  5. dry with materialThe organic phase is dried over MgSO4
  6. customThe purification

Sources & evidence

ORD record
ord-203905a7d77046488e114cc9db773bb7
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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