Sodium hydride → 6-fluoro-7-iodo-2-(2-methoxyethyl)-2H-pyrazolo[4,3-b]pyridine

HRID 1522580Notes

Reaction equation

HRID 1522580 reaction equation
[F:1][C:2]1[C:3]([I:11])=[C:4]2[NH:10][N:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:15][CH2:16][O:17][CH3:18]>CN(C=O)C.O.C(#N)C.O>[F:1][C:2]1[CH:7]=[N:6][C:5]2=[CH:8][N:9]([CH2:15][CH2:16][O:17][CH3:18])[N:10]=[C:4]2[C:3]=1[I:11]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 674703846-fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 674695816-fluoro-7-iodo-2-(2-methoxyethyl)-2H-pyrazolo[4,3-b]pyridineYield 28.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

6-Fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridine (150 mg, 0.570 mmol) was dissolved in DMF (5 mL) and sodium hydride (34.2 mg, 0.855 mmol) was added slowly, followed by 1-bromo-2-methoxyethane (0.080 ml, 0.855 mmol). After 90 minutes, the reaction was quenched with crushed ice and the reaction mixture was purified by preparative HPLC eluting with 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water on a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column) to give 6-fluoro-7-iodo-2-(2-methoxyethyl)-2H-pyrazolo[4,3-b]pyridine (52 mg, 28.4% yield) as white solid. MS [M+H] found 322.1

Workup

  1. customthe reaction was quenched with crushed ice
  2. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-0af92f06fa364deab63050908cfe44e1
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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