[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 10001170, compound

HRID 392159Notes

Reaction equation

HRID 392159 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][C:3](NCCCC)=[CH:2]1.BrC1C=CC(S(O[CH2:26][C@@H:27]2[O:41][C:31]3=[C:32]4[C:37](=[CH:38][CH:39]=[C:30]3[O:29][CH2:28]2)[N:36]=[C:35]([CH3:40])[CH:34]=[CH:33]4)(=O)=O)=CC=1>CS(C)=O.C(=O)(O)[O-].[Na+]>[O:1]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:9][C:8]=2[C:7]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][CH2:26][CH:27]2[O:41][C:31]3=[C:32]4[C:37](=[CH:38][CH:39]=[C:30]3[O:29][CH2:28]2)[N:36]=[C:35]([CH3:40])[CH:34]=[CH:33]4)=[CH:6]1

Participants

5

Reactant 2

HCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonateHCID 69365058HCID 69365058, compound

Product 1

HCID 10001170HCID 10001170, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-benzofuran-3-yl-butylamine (770 mg, 4.07 mmol) in 6 mL of anhydrous DMSO was added [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (611 mg mg, 1.36 mmol). The reaction mixture was heated to 50° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (3×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. Flash chromatography on SiO2 (5% MeOH/CH2Cl2) afforded 403 mg (74%) of the (S)-enantiomer of the title compound as a yellow oil. The fumarate salt was prepared, yielding 285 mg of a beige solid, m.p. 127-130° C.; MS (ESI) m/z 403 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with brine (3×30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-fba0bddba78a454586e3688672bc00bf
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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