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Tributyl(2,3-dihydrofuran-5-yl)stannane → 2-(3-methoxyphenyl)-9-(tetrahydrofuran-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

HRID 532916
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인쇄 미리보기

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HRID 532916 반응식
[O:1]1[CH2:5][CH2:4][CH:3]=[C:2]1[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][N:10]1[C:20](=[O:21])[CH2:19][N:18]=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[CH:16]=[C:11]12.IC1C=CC=C2C=1CCN1C(=O)CN=C(C3C=CC=C(OC)C=3)C=C12.C([Sn](CCCC)(CCCC)C1OCCC=1)CCC>O1CCOCC1.CCOC(C)=O.CCCCCCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([C:17]2[CH:16]=[C:11]3[C:12]4[C:7]([CH2:8][CH2:9][N:10]3[C:20](=[O:21])[CH2:19][N:18]=2)=[C:6]([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[CH:15]=[CH:14][CH:13]=4)[CH:27]=[CH:26][CH:25]=1
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참가 물질

8

반응물 3

HCID 14323397Tributyl(2,3-dihydrofuran-5-yl)stannaneHCID 867113559-iodo-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-oneHCID 867113619-(4,5-dihydrofuran-2-yl)-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

생성물 1

HCID 899795192-(3-methoxyphenyl)-9-(tetrahydrofuran-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 8900Heptane용매
HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

9-(4,5-dihydrofuran-2-yl)-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one. 57-1. A mixture of 9-iodo-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (Example 30) (1.0 g, 2.25 mmol), tributyl(4,5-dihydrofuran-2-yl)stannane (1.21 g, 3.38 mmol) and Pd(PPh3)4(0.13 g, 0.11 mmol) in 1,4-dioxane (10 mL) was heated in a microwave reactor at 150° C. for 90 min. The mixture was then diluted with AcOEt and filtered. The filtrate was concentrated in vacuo and the crude product obtained was purified by flash chromatography (SiO2, heptane to heptane/AcOEt 1:1) to give a brown solid, which was suspended in heptane and heated to reflux. The suspension was then allowed to cool to RT and then filtered. The filter cake was then dried in vacuo to afford the title compound (543 mg) as a beige solid. UPLC-MS: MS 387.2 (M+H+); UPLC rt 1.10 min.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe crude product obtained
  4. customwas purified by flash chromatography (SiO2, heptane to heptane/AcOEt 1:1)
  5. customto give a brown solid, which
  6. temperatureheated to reflux
  7. temperatureto cool to RT
  8. filtrationfiltered
  9. customThe filter cake was then dried in vacuo

출처 및 근거

ORD 기록
ord-7612c8319c6740cb8fa8721b213f4675
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853203B2

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