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Tris(furan-2-yl)phosphane → (5R)-3-(3-Fluoro-4-(6-(5-hydroxymethyl-4,5-dihydroisoxazol-3-yl)pyridin-3-yl)phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 747256
ノート
印刷プレビュー

反応式

HRID 747256 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]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1I.C[Sn](C)(C)[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH2:33][CH:32]([CH2:34][OH:35])[O:31][N:30]=2)=[N:27][CH:28]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[C:23]1[CH:28]=[N:27][C:26]([C:29]2[CH2:33][CH:32]([CH2:34][OH:35])[O:31][N:30]=2)=[CH:25][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 11257720(R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-oneHCID 59749487{3-[5-(Trimethylstannyl)pyridin-2-yl)-4,5-dihydroisoxazol-5-yl}methanol

生成物 1

HCID 59749476(5R)-3-(3-Fluoro-4-(6-(5-hydroxymethyl-4,5-dihydroisoxazol-3-yl)pyridin-3-yl)phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one収率 44.1%

試薬・触媒・溶媒 1

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒

反応条件

温度
90 °C

実験手順

(5R)-3-(3-Fluoro-4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (342 mg, 0.88 mM), {3-[5-(trimethylstannyl)pyridin-2-yl)-4,5-dihydroisoxazol-5-yl}methanol (300 mg, 0.88 mM), tris(dibenzylideneacetone) dipalladium (0)-chloroform adduct (91 mg, 0.088 mM, 0.1 equiv.) and tri-2-furylphosphine (41 mg, 0.176 mM, 0.2 equiv) were placed in a flask. The contents of the flask were degassed and placed under nitrogen. Anhydrous dioxane (5 ml) was added and the mixture was heated at 90° C. for 5 hours and then cooled to room temperature. Solvent was evaporated under reduced pressure and the residue was purified by chromatography (silica gel; elution with 5% methanol in dichloromethane) to give the title compound (170 mg).

後処理

  1. customThe contents of the flask were degassed
  2. additionAnhydrous dioxane (5 ml) was added
  3. temperaturecooled to room temperature
  4. customSolvent was evaporated under reduced pressure
  5. customthe residue was purified by chromatography (silica gel; elution with 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-62afe6c04ad242178b4aede3b1269c0f
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07396847B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート