Sodium Hydroxide → (6-bromo-pyridin-3-ylmethyl)-[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine

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Reaction Conditions

Reaction Steps

To 5-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (120, 80.0 mg, 0.200 mmol) in 2.00 mL of ethanol and 0.10 mL of acetic acid, 6-bromo-pyridine-3-carbaldehyde (121, 100.0 mg, 0.538 mmol) and silica supported cyanoborohydride (0.50 g, 1.21 mmol/g) were added. The reaction was heated at 110° C. for 25 minutes in microwave. Sodium hydroxide (2.0 mL, 6.0 M aqueous) was added and the reaction heated at 100° C. for 10 minutes in microwave, then poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-2002, 26.6 mg). MS (ESI) [M+H+]+=427.7, 429.7.

Provenance & Evidence