Isopropylamine → 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-isopropylpyrazolo[1,5-alpha]pyridin-5-amine

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Reaction Steps

4-[5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (0.1 g, 0.25 mmol) and isopropylamine were treated with rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, cesium carbonate and palladium (II) acetate as described in Example 2 to give, after purification by flash chromatography (1:1 hexanes-ethyl acetate), 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-isopropylpyrazolo[1,5-α]pyridin-5-amine (70 mg, 66%) as a solid. 1H-NMR (CDCl3): δ 8.17 (d, 1H), 7.9 (d, 1H), 7.58 (q, 2H), 7.4 (m, 1H), 7.15 (t, 2H), 6.24 (dd, 1H), 6.2 (d, 1H), 5.25 (broad s, 1H), 4.4 (m, 1H), 3.95 (d, 1H), 3.75 (m, 1H), 2.1 (m, 2H), 1.5–1.8 (m, 6H), 1.30 (d, 6H); 19F-NMR (CDCl3): δ −113.45; MS m/z 431 (M+1).

Provenance & Evidence