Ethyl bromoacetate → Acetic acid, 2-[(3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy]-, ethyl ester

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Reaction Conditions

Reaction Steps

3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (720 mg, 3.64 mmol) was dissolved in DMF (5 ml) at rt. Then, DIPEA (1.04 g, 8.0 mmol) and ethyl 2-bromoacetate (0.60 ml, 5.5 mmol) were added and the mixture heated at 90° C. After 1 h, the mixture was cooled to rt, the solvent removed under reduced pressure and the residue purified by column chromatography (eluent 70% hexane in EtOAc) to yield 664 mg (64%) of the title compound. [1H-NMR (DMSO-d6, 400 MHz) δ 6.67 (s, 1H), 4.98 (s, 2H) 4.17 (q, 2H), 3.84 (s, 3H), 2.62 (s, 3H), 1.19 (t, 3H); HPLC-MS RtJ=1.13 min; [M+H]+=284.0, 286.0

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