Tris(furan-2-yl)phosphane → HCID 59749445, 화합물

HRID 747235

반응식

HRID 747235 반응식
[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Sn](C)(C)C)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:36][C@H:35]([CH2:37][N:38]3[CH:42]=[C:41]([CH3:43])[N:40]=[N:39]3)[O:34][C:33]2=[O:44])=[CH:28][CH:27]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:36][C@H:35]([CH2:37][N:38]5[CH:42]=[C:41]([CH3:43])[N:40]=[N:39]5)[O:34][C:33]4=[O:44])=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 597494295-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]4,5-dihydroisoxazoleHCID 59749434(5R)-3-(4-Iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

생성물 1

HCID 59749445HCID 59749445, 화합물수율 28.3%

시약·촉매·용매 2

HCID 44556509Tris(dibenzylideneacetone) palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]4,5-dihydroisoxazole (0.70 g, 1.6 mmol), (5R)-3-(4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (0.5 g, 1.29 mmol), tri-2-furyl phosphine (0.06 g, 0.26 mmol) and tris(dibenzylideneacetone)palladium (0) (0.12 g, 0.13 mmol) were dissolved in 1,4-dioxane (5 ml) and degassed three times. The mixture was then heated to 90° C. and stirred for 18 hr. LCMS indicated that the reaction was not yet complete, so it was cooled and an additional (0.12 g, 0.13 mmol) of tris(dibenzylidene acetone) palladium (0) was added, the mixture degassed and reheated to 110° C. for 3 hours, and 25° C. for 40 hours. The solution was concentrated in vacuo and purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.2 g of the desired product as a yellow solid.

후처리

  1. customdegassed three times
  2. temperatureso it was cooled
  3. customthe mixture degassed
  4. waitreheated to 110° C. for 3 hours
  5. wait25° C. for 40 hours
  6. concentrationThe solution was concentrated in vacuo
  7. custompurified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

출처 및 근거

ORD 기록
ord-aa766d7d8b7b4900aa80758113d2bce9
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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