N-Iodosuccinimide → HCID 69077347, 화합물

HRID 1916623노트

반응식

HRID 1916623 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 69077347HCID 69077347, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-203905a7d77046488e114cc9db773bb7
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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