Sodium Carbonate → HCID 24985251, Verbindung

3-(4-Iodo-benzyl)-1-oxa-3-aza-spiro[4.5]decan-2-one (55 mg, 0.148 mmol) and benzylmopholine-2-boronic acid (49 mg, 0.222 mmol) were mixed in ethylene glycol dimethyl ether (1 mL) and sodium carbonate (2M) aqueous solution (1 mL). Tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (17 mg, 0.0148 mmol) was added and the reaction mixture was heated at 100˜110° C. for 1˜1.5 hours. The reaction was diluted with dichloromethane (DCM), washed with water (4 mL) and brine (4 mL). The organic phase was separated, dried over anhydrous sodium sulfate and concentrated. The crude residue was purified on silica gel eluting with 5-30% ethyl acetate in hexane to give the product as off-white solid (52 mg, 83%). 1H NMR (300 MHz, CDCl3): δ 7.49 (m, 1H), 7.42 (d, 2H), 7.32 (m, 5H), 4.5 (s, 2H), 3.65 (t, 4H), 3.39 (s, 2H), 3.18 (s, 2H), 2.36 (t, 4H), 1.82 (m, 4H), 1.54 (m, 6H).

1. temperaturethe reaction mixture was heated at 100˜110° C. for 1˜1.5 hours
2. washwashed with water (4 mL) and brine (4 mL)
3. customThe organic phase was separated
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated
6. customThe crude residue was purified on silica gel eluting with 5-30% ethyl acetate in hexane

ORD-Eintrag

ord-175fe6edd2cc4854944d4916159c38a3

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07485722B2