3-Methyl-5-(tributylstannyl)isoxazole → (5R)-3-(3-fluoro-4-(3-methylisoxazol-5-yl)phenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one

HRID 1371822노트

반응식

HRID 1371822 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])[CH:5]=[CH:6][C:7]=1I.C([Sn](CCCC)(CCCC)[C:27]1[O:31][N:30]=[C:29]([CH3:32])[CH:28]=1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])[CH:5]=[CH:6][C:7]=1[C:27]1[O:31][N:30]=[C:29]([CH3:32])[CH:28]=1

참가 물질

5

반응물 2

HCID 27632553-Methyl-5-(tributylstannyl)isoxazoleHCID 58778315(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one2회

생성물 1

HCID 9950622(5R)-3-(3-fluoro-4-(3-methylisoxazol-5-yl)phenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one수율 88.3%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매2회

반응 조건

온도
100 °C

실험 절차

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 2, 2.08 g, 5.20 mmol) was dissolved in anhydrous 1,4-dioxane (10 ml) and degassed and placed under argon. Bis(triphenylphospine)palladium(II) chloride (0.145 g, 0.210 mmol) was added followed by dropwise addition of 5-(tributylstannyl)-3-methylisoxazole (2.41 g, 6.50 mmol) (Sakamoto, T. et al., Tetrahedron, 47, 28, 5111–5118) in 1,4-dioxane (2 ml). The reaction was degassed and heated at 100° C. for 48 hours. The solvent was removed under vacuum and the residue was dissolved in acetonitrile and washed with hexanes. The acetonitrile layer was concentrated to give a yellow solid (1.64 g) that was adsorbed onto silica gel and purified by flash chromatography using 10–20% acetone/dichloromethane. Relevant fractions were concentrated to give an off-white solid (1.50 g).

후처리

  1. customdegassed
  2. customThe reaction was degassed
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in acetonitrile
  5. washwashed with hexanes
  6. concentrationThe acetonitrile layer was concentrated

출처 및 근거

ORD 기록
ord-85542233bcfb4a2d80b83e741f72de20
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157482B2

반응 노트

불러오는 중…