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Tris(furan-2-yl)phosphane → HCID 24802856, 화합물

HRID 1690720
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HRID 1690720 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.O1C=CC=C1P(C1O[CH:33]=[CH:34][CH:35]=1)C1OC=CC=1.C([Sn](CCCC)(CCCC)C1CC1)CCC>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]>[CH:34]1([C:2]2[N:6]([CH:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10](=[O:17])[O:9][C:8]3([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=2)[CH2:35][CH2:33]1
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참가 물질

6

반응물 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 10947505CyclopropyltributylstannaneHCID 57781136HCID 57781136, 화합물

생성물 1

HCID 24802856HCID 24802856, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
95 °C

실험 절차

To a flask charged with 4-(5-iodo-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (350 mg, 0.95 mmol) (Example 2b), tris(dibenzylideneacetone)dipalladium(0) (98 mg, 0.095 mmol) and trifuran-2-yl-phosphane (33 mg, 0.142 mmol) and flushed with N2 is added tributylcyclopropyltin (1.89 g, 5.7 mmol) in degassed N-methylpyrrolidinone (3 mL). The mixture is degassed for 15 min and heated to 95° C. for 25 h. The reaction mixture is quenched with water and extracted with ethyl acetate three times. The organic phase is combined, dried over sodium sulfate, concentrated and the residue is purified by semi-preparative reverse phase HPLC to give 4-(5-cyclopropyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as white solid; (ESI) m/z 283.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 0.69 (s, 1 H), 0.81 (br. s, 1 H), 1.09 (br. s, 2 H), 1.29 (s, 3 H), 1.56 (s, 3 H), 1.94 (br. s, 1 H), 5.78 (s, 1 H), 6.68 (s, 1 H), 7.14 (br. s, 1 H), 7.42 (d, J=7.1 Hz, 1 H), 7.63 (td, J=7.6, 1.3 Hz, 1 H), 7.75 (td, J=7.6, 1.3 Hz, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1 H).

후처리

  1. customflushed with N2
  2. customThe mixture is degassed for 15 min
  3. customThe reaction mixture is quenched with water
  4. extractionextracted with ethyl acetate three times
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is purified by semi-preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-b0c1df385c7d4390a9f8f0db418fb067
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153674B2

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