Dimethylformamide → HCID 66759972, compound
Reaction equation
[H-].[Na+].[Cl:3][C:4]1[O:14][C:7]2=[C:8]([NH2:13])[N:9]=[CH:10][C:11]([I:12])=[C:6]2[CH:5]=1.CI.[CH3:17][N:18]([CH:20]=O)[CH3:19]>>[Cl:3][C:4]1[O:14][C:7]2=[C:8]([NH:13][CH3:17])[N:9]=[CH:10][C:11]([I:12])=[C:6]2[CH:5]=1.[Cl:3][C:4]1[O:14][C:7]2=[C:20]([N:18]([CH3:17])[CH3:19])[N:9]=[CH:10][C:11]([I:12])=[C:6]2[CH:5]=1Participants
Procedure
To a cooled (0° C.) suspension of sodium hydride (15 mg, 0.37 mmol) in DMF (200 μL) was added dropwise a solution of 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (100 mg, 0.340 mmol) in DMF (1 mL). After 5 min, methyl iodide (23 μL, 0.37 mmol) was added and the reaction stirred at room temperature for 2 h. The reaction was then quenched with water (30 mL). The quenched mixture was extracted with dichloromethane (2×10 mL). The combined organic fractions were washed with water (1×10 mL) and brine (1×10 mL), dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (5 to 25% ethyl acetate:heptane) afforded 18 mg (17%) of 2-chloro-4-iodo-N-methylfuro[2,3-c]pyridin-7-amine and 44 mg (40%) of 2-chloro-4-iodo-N,N-dimethylfuro[2,3-c]pyridin-7-amine as off-white white solids.
Workup
- temperatureTo a cooled
- customThe reaction was then quenched with water (30 mL)
- extractionThe quenched mixture was extracted with dichloromethane (2×10 mL)
- washThe combined organic fractions were washed with water (1×10 mL) and brine (1×10 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification by ISCO chromatography (5 to 25% ethyl acetate:heptane)
Sources & evidence
- ORD record
- ord-de42a204014f4535889a09ecc8e02717
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
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