Triphenylarsine → HCID 22022972, 화합물

HRID 1793679노트

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HRID 1793679 반응식
C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:22]=[C:23]([C:28]2[CH2:32][CH:31]([CH2:33][N:34]([C:42]3[CH:46]=[CH:45][O:44][N:43]=3)[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[O:30][N:29]=2)[CH:24]=[CH:25][C:26]=1I.[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][C:57]([Sn](C)(C)C)=[CH:56][CH2:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48]>CN1CCCC1=O.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.[Pd].[Pd]>[F:20][C:21]1[CH:22]=[C:23]([C:28]2[CH2:32][CH:31]([CH2:33][N:34]([C:42]3[CH:46]=[CH:45][O:44][N:43]=3)[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[O:30][N:29]=2)[CH:24]=[CH:25][C:26]=1[C:57]1[CH2:58][CH2:59][N:54]([C:52]([O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:53])[CH2:55][CH:56]=1

참가 물질

6

반응물 3

HCID 11773TriphenylarsineHCID 22022989HCID 22022989, 화합물HCID 69521876(5RS)-3-(3-Fluoro-4-iodophenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydro-isoxazole

생성물 1

HCID 22022972HCID 22022972, 화합물수율 48.9%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Tris(dibenzylideneacetone)dipalladium (141 mg, 0.154 mM) and triphenylarsine (188 mg, 0.616 mM) were dissolved in degassed N-methylpyrrolidone (40 ml) under nitrogen, and stirred for 15 minutes. (5RS)-3-(3-Fluoro-4-iodophenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydro-isoxazole (1.5 g, 3.08 mM) and 1-t-butoxycarbonyl-4-trimethylstannyl-1,2,5,6-tetrahydropyridine (1.99 g, 4.62 mM) were added, and the reaction heated at 70–80° for 18 hours. The mixture was filtered through celite and evaporated to dryness, and the residue chromatographed on a 40 g silica Biotage column, eluting with 25% ethyl acetate in isohexane. Relevant fractions were combined to give the desired product (817 mg).

후처리

  1. temperaturethe reaction heated at 70–80° for 18 hours
  2. filtrationThe mixture was filtered through celite
  3. customevaporated to dryness
  4. customthe residue chromatographed on a 40 g silica Biotage column
  5. washeluting with 25% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-5fe6025313db441eb2d02197eab1cf91
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07081538B1

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