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Cesium carbonate → 4-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-1-(2-propylsulfanyl-pyrimidin-4-yl)-1H-indole

HRID 237431
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HRID 237431 반응식
[CH2:1]([S:4][C:5]1[N:10]=[C:9]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[CH:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)[CH2:2][CH3:3].[O:21]=[S:22]1(=[O:39])[CH2:26][CH2:25][CH:24]([CH2:27]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[O:21]=[S:22]1(=[O:39])[CH2:26][CH2:25][CH:24]([CH2:27][O:20][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[CH:13]=[CH:12][N:11]3[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH2:1][CH2:2][CH3:3])[N:10]=2)[CH2:23]1
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HCID 10796Cesium carbonateHCID 18801509(1,1-Dioxo-1lambda6-thiolan-3-yl)methyl 4-methylbenzene-1-sulfonateHCID 585421691-(2-Propylsulfanyl-pyrimidin-4-yl)-1H-indol-4-ol

생성물 1

HCID 585421654-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-1-(2-propylsulfanyl-pyrimidin-4-yl)-1H-indole수율 129.7%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
70 °C

실험 절차

1-(2-Propylsulfanyl-pyrimidin-4-yl)-1H-indol-4-ol (1.56 g) and toluene-4-sulfonic acid 1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethyl ester (2.37 g) were added to NMP (20 mL), followed by cesium carbonate (5.08 g). The mixture was stirred at 70° C. for 60 hours, after which solvent was removed by distillation. The residue was diluted with 1N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give 2.96 g of 4-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-1-(2-propylsulfanyl-pyrimidin-4-yl)-1H-indole.

후처리

  1. customafter which solvent was removed by distillation
  2. additionThe residue was diluted with 1N HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f395cc63e2af4a26b814aac9d53cebe2
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642601B2

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