Water → 6-Cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)-4-(indol-5-yloxy)quinoline

HRID 2222395Notes

Reaction equation

HRID 2222395 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]1)[N:5]=[CH:4][CH:3]=[C:2]2[O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2)#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 597122364-Chloro-6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline

Product 1

HCID 101164466-Cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)-4-(indol-5-yloxy)quinolineYield 22.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-chloro-6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline (100 mg, 0.26 mmol), (prepared as described for the starting material in Example 1), 5-hydroxyindole (42 mg, 0.32 mmol) and cesium carbonate (129 mg, 0.39 mmol) in DMF (1 ml) was stirred for 10 minutes at ambient temperature followed by 1.5 hours at 70° C. After cooling, water (5 ml) was added. The precipitate was filtered, washed with water and dried under vacuum. The solid was purified by column chromatography, eluting with methanol/methylene chloride/ethyl acetate (5/45/50) to give 6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)-4-(indol-5-yloxy)quinoline (28 mg, 22%).

Workup

  1. custom(prepared
  2. waitfollowed by 1.5 hours at 70° C
  3. temperatureAfter cooling
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried under vacuum
  7. customThe solid was purified by column chromatography
  8. washeluting with methanol/methylene chloride/ethyl acetate (5/45/50)

Sources & evidence

ORD record
ord-4eb35255dd0f4e48b00ced163adb221d
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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