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

HRID 237431Notes

Reaction equation

HRID 237431 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f395cc63e2af4a26b814aac9d53cebe2
Source dataset
uspto-grants-2014_02
Patent number
US08642601B2

Reaction notes

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