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

HRID 219287

反応式

HRID 219287 の反応式
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

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cb12bebbeccc4a719bb91e95332a4562
出典データセット
uspto-grants-2012_06
特許番号
US08198448B2

関連ノート

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