Cesium carbonate → 7-iodo-1-(2-methoxyethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 1522610노트

반응식

HRID 1522610 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.Br[CH2:12][CH2:13][O:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O.C(#N)C.O>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[N:10]=2)[N:5]=[CH:6][CH:7]=1.[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][O:14][CH3:15])[C:3]=12

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 178506553HCID 178506553, 화합물

생성물 2

HCID 674704397-iodo-1-(2-methoxyethyl)-1H-pyrazolo[4,3-b]pyridine수율 24.25%HCID 867043677-iodo-2-(2-methoxyethyl)-2H-pyrazolo[4,3-b]pyridine수율 24.25%

시약·촉매·용매 3

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

반응 조건

온도
120 °C

실험 절차

7-Iodo-2H-pyrazolo[4,3-b]pyridine (100 mg, 0.408 mmol), 1-bromo-2-methoxyethane (56.7 mg, 0.408 mmol) and cesium carbonate (266 mg, 0.816 mmol) were combined in DMF (5 mL). The mixture was heated at 120° C. for 1 hour, then cooled and purified by preparative HPLC using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-70% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water to give 7-iodo-2-(2-methoxyethyl)-2H-pyrazolo[4,3-b]pyridine (30 mg, 24.25% yield) and 7-iodo-1-(2-methoxyethyl)-1H-pyrazolo[4,3-b]pyridine (30 mg, 24.25% yield). MS [M+H] found 304.1.

후처리

  1. temperaturecooled
  2. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-bf54db48e38744b3a439fb46618bb5f7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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