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

HRID 219240

반응식

HRID 219240 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매2회HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

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 C14H13N2O4 (M+H) 273.1, found 273.3.

후처리

  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

출처 및 근거

ORD 기록
ord-843fc7c11bf545a6a228448a925926ca
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

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