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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204455Generated: October 31, 2026

Sodium hydride → HCID 58009950, compound

https://huagongshe.com/reaction/2204455

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant4-t-Butylbenzenesulfonyl chlorideHCID 139882—
Reactant2-bromo-5H-pyrrolo[2,3-b]pyrazineHCID 25067308—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 58009950HCID 5800995091.1%

Reaction Conditions

Temperature5 °C

Reaction Steps

A solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.00 g, 25.2 mmol, Ark Pharm) in DMF (150 mL) was cooled in an ice bath to about 0° C. and then NaH (60% dispersion in mineral oil, 1.21 g, 30.3 mmol) was added. After about 15 min, 4-tert-butylbenzene-1-sulfonyl chloride (6.46 g, 27.8 mmol) was added. The reaction was maintained between about 0-10° C. for about 2 h. Then, the reaction was diluted with water (200 mL) to give a yellow suspension. The solid was collected by vacuum filtration, while washing with additional water (100 mL), and dried in a vacuum oven at about 70° C. to give 2-bromo-5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (9.05 g, 91%): LC/MS (Table 2, Method a) Rt=3.05 min; MS m/z: 394/396 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365579B2
Source datasetuspto-grants-2016_06
ORD IDord-3b6e01724b594684ac7c2983058ab20b
Source noteuspto-grants-2016_06