1,4-Dioxane → Methyl 2-(5-(3-methylisoxazol-5-yl)furo[3,2-b]pyridin-3-yl)acetate

HRID 2176654ノート

反応式

HRID 2176654 の反応式
Cl[C:2]1[N:7]=[C:6]2[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:9][O:10][C:5]2=[CH:4][CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:50][C:51]1[CH:55]=[C:54]([Sn](CCCC)(CCCC)CCCC)[O:53][N:52]=1.O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.C(Cl)Cl>[CH3:50][C:51]1[CH:55]=[C:54]([C:2]2[N:7]=[C:6]3[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:9][O:10][C:5]3=[CH:4][CH:3]=2)[O:53][N:52]=1

参加物

8

反応物 4

HCID 312751,4-DioxaneHCID 27632553-Methyl-5-(tributylstannyl)isoxazoleHCID 10198435Methyl 2-(5-chlorofuro[3,2-b]pyridin-3-yl)acetateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

生成物 1

HCID 57690995Methyl 2-(5-(3-methylisoxazol-5-yl)furo[3,2-b]pyridin-3-yl)acetate収率 96.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A sealable flask was charged with methyl 2-(5-chlorofuro[3,2-b]pyridin-3-yl)acetate, palladium (II) acetate (49.8 mg, 222 μmol), X-Phos (211 mg, 443 μmol), and 3-methyl-5-(tributylstannyl)isoxazole (1319 mg, 3546 μmol). The flask was sealed and dioxane (20 mL) was added. The mixture was sparged with N2 for 10 min, then heated at 100° C. for 48 h. The mixture was cooled to rt and concentrated for purification by MPLC (Teledine Isco combiFlash Companion). The crude residue was taken up in minimal CH2Cl2 and absorbed onto a 25 g loading cartridge and passed through a Redi-Sep®, pre-packed silica gel column (40 g) using 98:2 CH2Cl2:MeOH to 90:10 CH2Cl2: MeOH to afford methyl 2-(5-(3-methylisoxazol-5-yl)furo[3,2-b]pyridin-3-yl)acetate (581 mg, 96.3% yield). LRMS (ESI) m/z calcd for C4H113N2O4 (M+H) 273.1. found 273.3.

後処理

  1. customThe flask was sealed
  2. customThe mixture was sparged with N2 for 10 min
  3. temperatureThe mixture was cooled to rt
  4. concentrationconcentrated for purification by MPLC (Teledine Isco combiFlash Companion)
  5. customabsorbed onto a 25 g loading cartridge

出典と根拠

ORDレコード
ord-52086ca3e46849b9b67564fb6bd3128a
出典データセット
uspto-grants-2015_06
特許番号
US09066954B2

反応ノート

読み込み中…