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 1371822ノート

反応式

HRID 1371822 の反応式
[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

参加物

5

反応物 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-one2 回

生成物 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-one収率 88.3%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-85542233bcfb4a2d80b83e741f72de20
出典データセット
uspto-grants-2007_01
特許番号
US07157482B2

反応ノート

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