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Chloroform → HCID 57781097, 화합물

HRID 1690717
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HRID 1690717 반응식
I[C:2]1[N:6]([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]2([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC.C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OC(C)C)(=O)C.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].CN(C=O)C>[CH:20]([C:2]1[N:6]([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]2([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1)=[CH2:21]
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참가 물질

8

반응물 4

HCID 6212ChloroformHCID 11776TriphenylphosphineHCID 53438229Tri(butyl)vinyltinHCID 57781136HCID 57781136, 화합물

생성물 1

HCID 57781097HCID 57781097, 화합물

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium
촉매
HCID 6228Dimethylformamide용매
HCID 7915Isopropyl Acetate용매

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온도
90 °C

실험 절차

DMF (30 mL) is added to 4-(5-iodo-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (1.62 g, 4.18 mmol) (Example 2b), tributylvinyltin (2.40 g, 8.36 mmol), Pd2 dba3.CHCl3 (0.087 g, 0.084 mmol) and triphenylphosphine (0.089 g, 0.334 mmol) under nitrogen. The mixture is heated to 90° C., to give a clear tan solution. After 3 h, the mixture is cooled down, diluted with isopropyl acetate and washed twice with water and brine. The combined organic phase is dried over magnesium sulfate and filtered through a cotton plug. The residue is purified by silica gel flash chromatography (10% wt silica gel/KF, elution with dichloromethane-methanol, 49:1 to 24:1) to give 4-(5-vinyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a yellow solid; MS (ESI) m/z 269.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.20 (s, 3 H), 1.51 (s, 3 H), 5.42 (br. s, 1 H), 5.69 (s, 1 H), 5.81 (br. s, 1 H), 6.95 (br. s, 1 H), 7.14 (br. s, 1H), 7.21 (s, 1 H), 7.42 (d, J=7.6 Hz, 1 H), 7.58-7.69 (m, 1 H), 7.70-7.80 (m, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1 H).

후처리

  1. customto give a clear tan solution
  2. temperaturethe mixture is cooled down
  3. washwashed twice with water and brine
  4. dry with materialThe combined organic phase is dried over magnesium sulfate
  5. filtrationfiltered through a cotton plug
  6. customThe residue is purified by silica gel flash chromatography (10% wt silica gel/KF, elution with dichloromethane-methanol, 49:1 to 24:1)

출처 및 근거

ORD 기록
ord-3a17397656f849f08f2ad6b97fa02c64
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153674B2

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