Morpholine → 6-Iodo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline

HRID 13658Notes

Reaction equation

HRID 13658 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH3:13])[C:3]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:2]2[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 120016244-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

Product 1

HCID 120018066-Iodo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinolineYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline (compound of example D.2) (1 g, 2.62 mmol), morpholine (274 mg, 3.1 mmol) and N,N-diisopropyl ethyl amine (406 mg, 3.1 mmol) were heated at 100° C. in dry N,N-dimethylformamide (10 mL) for 30 min. The reaction mixture was evaporated to dryness, and the residue extracted with dichloromethane, 10% Na2CO3 and sat. NaCl. The crude product was purified by chromatography on silica gel in dichloromethane/ethyl acetate 5:1. One obtained 913 mg (80%) of a yellow foam. MS: m/z=433 (M+H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionthe residue extracted with dichloromethane, 10% Na2CO3 and sat. NaCl
  3. customThe crude product was purified by chromatography on silica gel in dichloromethane/ethyl acetate 5:1

Sources & evidence

ORD record
ord-57f0dd3722d6450a8ffa7ad78ef9ed99
Source dataset
uspto-grants-2010_06
Patent number
US07728142B2

Reaction notes

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