Tris(furan-2-yl)phosphane → (5R)-3-(3-Fluoro-4-{5-[5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747250노트

반응식

HRID 747250 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](C)(C)[C:24]1[S:28][C:27]([C:29]2[CH2:33][CH:32]([CH2:34][OH:35])[O:31][N:30]=2)=[CH:26][CH:25]=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]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])[CH:5]=[CH:6][C:7]=1[C:24]1[S:28][C:27]([C:29]2[CH2:33][CH:32]([CH2:34][OH:35])[O:31][N:30]=2)=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 58778315(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-oneHCID 59749480{3-[5-(Trimethylstannyl)thien-2-yl]4,5-dihydroisoxazol-5-yl}methanol

생성물 1

HCID 59749409(5R)-3-(3-Fluoro-4-{5-[5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one수율 60.6%

시약·촉매·용매 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)촉매

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온도
90 °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 (232 mg, 0.58 mM), {3-[5-(trimethylstannyl)thien-2-yl]4,5-dihydroisoxazol-5-yl}methanol (200 mg, 0.58 mM), tris(dibenzylideneacetone) dipalladium (0)-chloroform adduct (60 mg, 0.058 mM) and tri-2-furylphosphine (27 mg, 0.116 mM) were placed in a flask. The solids were degassed and placed under nitrogen. Anhydrous dioxane (5 ml) was added and the suspension was heated at 90° C. for 16 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give the title compound (160 mg).

후처리

  1. customThe solids were degassed
  2. additionAnhydrous dioxane (5 ml) was added
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-f923f9661f0d4f08ad6c5fabc08ad307
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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