Dichloromethane → 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

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Reaction Steps

Prepared according to the procedure of Example 1, Step D, substituting 1-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-3-methyl-1H-pyrazolo[3,4-b]pyridine (7.4 g, 18 mmol) for 1-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine, and substituting EtOAc for DCM during the workup. The product was obtained as a gum (7.2 g, 94%) and used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J=5 Hz, 1H), 7.30 (d, J=9 Hz, 2H), 7.00 (m, 1H), 6.82 (d, J=9 Hz, 2H), 6.54 (m, 1H), 6.48 (m, 1H), 6.16 (d, J=5 Hz, 1H), 5.55 (s, 2H), 3.83 (br s, 2H), 3.75 (s, 3H), 2.71 (s, 3H).

Provenance & Evidence