1,4-Dioxane → 2,3-Difluoro-5-(3-methylisoxazol-5-yl)pyridine

HRID 219287

반응식

HRID 219287 반응식
Cl[C:2]1[CH:3]=[C:4]([F:9])[C:5]([F:8])=[N:6][CH:7]=1.[CH3:10][C:11]1[CH:15]=[C:14]([Sn](CCCC)(CCCC)CCCC)[O:13][N:12]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O1CCOCC1>>[F:8][C:5]1[C:4]([F:9])=[CH:3][C:2]([C:14]2[O:13][N:12]=[C:11]([CH3:10])[CH:15]=2)=[CH:7][N:6]=1

참가 물질

5

반응물 4

HCID 312751,4-DioxaneHCID 27632553-Methyl-5-(tributylstannyl)isoxazoleHCID 27832485-Chloro-2,3-difluoropyridineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

생성물 1

HCID 580155342,3-Difluoro-5-(3-methylisoxazol-5-yl)pyridine수율 55.4%

반응 조건

온도
100 °C

실험 절차

A 330 mL pressure vessel was charged with 5-chloro-2,3-difluoropyridine (5.00 g, 33.4 mmol), 3-methyl-5-(tributylstannyl)isoxazole (14.9 g, 40.1 mmol), XPhos (2.23 g, 4.68 mmol), PdOAc2 (0.526 g, 2.34 mmol), and 1,4-dioxane (167 ml, 33.4 mmol), flushed with argon, sealed, then heated at 100° C. for 16 hours. The mixture was concentrated; the black oil was absorbed onto silica gel and purified by MPLC, eluting with 20% EtOAc in hexanes isocratic to yield an orange solid; this was triturated with hexanes to give 2,3-difluoro-5-(3-methylisoxazol-5-yl)pyridine (3.6278 g, 55.3% yield) as a yellow solid.

후처리

  1. customflushed with argon
  2. customsealed
  3. concentrationThe mixture was concentrated
  4. customthe black oil was absorbed onto silica gel
  5. custompurified by MPLC
  6. washeluting with 20% EtOAc in hexanes isocratic
  7. customto yield an orange solid
  8. customthis was triturated with hexanes

출처 및 근거

ORD 기록
ord-cb12bebbeccc4a719bb91e95332a4562
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

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