4-Toluenesulfonyl chloride → HCID 59540985, compound

Participants

Reaction Steps

2-(3,4-Dimethoxy-phenyl)-7-iodo-5H-pyrrolo[2,3-b]pyrazine was prepared starting from 2-bromo-5H-pyrrolo[2,3-b]pyrazine and 3,4-dimethoxyphenylboronic acid. To a 0° C. solution of 2-(3,4-dimethoxy-phenyl)-7-iodo-5H-pyrrolo[2,3-b]pyrazine (821 mg, 2.1 mmol) in THF (20 mL) was added NaH (55% dispersion in mineral oil, 168 mg, 3.85 mmol) portionwise and the resultant mixture was stirred for 15 min, treated with TsCl (736 mg, 3.85 mmol), stirred overnight at room temperature, and poured into water and EtOAc. A yellow solid precipitated and the heterogeneous biphasic mixture was filtered to afford 680 mg (39%) of 2-(3,4-dimethoxy-phenyl)-7-iodo-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine as a yellow solid.

Provenance & Evidence