Sodium hydride → 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine

HRID 1522601노트

반응식

HRID 1522601 반응식
[I:1][C:2]1[C:3]2[C:4](=[CH:8][NH:9][N:10]=2)[N:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>CN(C=O)C.O.C(#N)C.O>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:10]=2)[N:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178506553HCID 178506553, 화합물

생성물 1

HCID 674695617-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine수율 20.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

7-Iodo-2H-pyrazolo[4,3-b]pyridine (1 g, 4.08 mmol) and sodium hydride (0.196 g, 8.16 mmol) were combined in DMF (15 mL) at room temperature. The mixture was stirred at room temperature for 10 minutes and 1-(chloromethyl)-4-methoxybenzene (0.554 ml, 4.08 mmol) was added. The mixture was stirred at room temperature for 1 hour the quenched with ice water and purified by preparative HPLC using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-90% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water to give the 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (300 mg, 20.1% yield) as a white powder. MS [M+H] found 366.1.

후처리

  1. stirringThe mixture was stirred at room temperature for 1 hour the
  2. customquenched with ice water
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-f42cffc50f3546db991179c615b2bc8a
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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