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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 921563Generated: October 30, 2026

Dimethylformamide → HCID 67501039, compound

https://huagongshe.com/reaction/921563

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl iodideHCID 6328—
ReactantEthyl AcetateHCID 8857—
ReactantSodium hydrideHCID 24758—
ReactantHCID 67501755HCID 67501755—
SolventWaterHCID 962—
ProductHCID 67501039HCID 6750103912%

Reaction Steps

Compound (107a) (0.08 g) and iodomethane (0.16 mL) were dissolved in DMF, and sodium hydride (0.028 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0° C., followed by stirring at room temperature for 1 hr. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away to obtain 3-(dimethylamino)-4-(4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile, which was used in the subsequent reaction without being purified. According to Example 107(2), compound (108) (0.014 g, the third stage yield: 12%) was prepared using 3-(dimethylamino)-4-(4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile instead of compound (107a).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273045B2
Source datasetuspto-grants-2016_03
ORD IDord-9860a40c9fb243039f82434bf539632f
Source noteuspto-grants-2016_03