2-Bromo-5-chloropyridine → HCID 58580279、化合物

反応式

[I-].[C:2]([O:10][CH2:11][Zn+])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:2]([O:10][CH2:11][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

実験手順

Title compound was prepared according to the procedure described in: Hasnik, Z.; Silhar, P.; Hocek, M. Synlett 2008, 4, 543. A solution of (benzoyloxymethyl)zinc(II) iodide Part B (2.17 mL, 1.949 mmol) was added to a solution of 2-bromo-5-chloropyridine (125 mg, 0.650 mmol) and Pd(PPh3)4 (37.5 mg, 0.032 mmol) in THF (1.30 mL). The reaction mixture was stirred at RT for 5 h at which point it was quenched with 1M NaH2PO4 (30 mL) The solid formed was filtered and washed well with water. The filtrate was extracted with DCM (3×25 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated. The crude product was subjected to flash chromatography (silica gel/hexanes-EtOAc 100:0 to 50:50 gradient) to afford (5-chloropyridin-2-yl)methyl benzoate 16C (101 mg, 63% yield) as an off-white solid. LC-MS, [M+H]+=248. HPLC-Method 8; 3.30 min.