Cesium carbonate → HCID 59730752, compound

HRID 130679Notes

Reaction equation

HRID 130679 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][C:18]1[O:19][C:20]2[CH:26]=[C:25]([O:27][C:28]3[C:37]4[C:32](=[CH:33][C:34]([OH:38])=[CH:35][CH:36]=4)[N:31]=[CH:30][CH:29]=3)[CH:24]=[CH:23][C:21]=2[CH:22]=1>CC#N.[Cl-].[Na+].O>[CH3:17][C:18]1[O:19][C:20]2[CH:26]=[C:25]([O:27][C:28]3[C:37]4[C:32](=[CH:33][C:34]([O:38][CH2:3][CH2:4][N:5]5[CH2:10][CH2:9][O:8][CH2:7][CH2:6]5)=[CH:35][CH:36]=4)[N:31]=[CH:30][CH:29]=3)[CH:24]=[CH:23][C:21]=2[CH:22]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 136090308HCID 136090308, compound

Product 1

HCID 59730752HCID 59730752, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 4-(2-Chloro-ethyl)-morpholine hydrochloride (153 mg, 0.82 mmol) and Cesium Carbonate (537 mg, 1.65 mmol) in CH3CN (2 ml) was stirred at room temperature for 1 hr. The 4-(2-Methyl-benzofuran-6-yloxy)-quinolin-7-ol 126-D (120 mg, 0.41 mmol) in CH3CN (2 ml) was added and the reaction was heated to reflux for 2 hr. The bright yellow reaction was cooled, poured into brine, and extracted with EtOAc (2 times). The combined organic layers were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 10% MeOH in EtOAc/CH2Cl2 (1:1). This gave slightly impure material which was re-purified by HPLC to give 110 mg (42%) of 4-(2-Methyl-benzofuran-6-yloxy)-7-(2-morpholin-4-yl-ethoxy)-quinoline 126 as the bis TFA salt.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hr
  3. customThe bright yellow reaction
  4. temperaturewas cooled
  5. extractionextracted with EtOAc (2 times)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on silica gel eluting with 10% MeOH in EtOAc/CH2Cl2 (1:1)
  10. customThis gave slightly impure material which
  11. customwas re-purified by HPLC

Sources & evidence

ORD record
ord-82d19decf7404b42a01deb1e9c4b1434
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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