Sodium hydride → HCID 69694285, compound

HRID 896698Notes

Reaction equation

HRID 896698 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11](=[O:47])[C:12]([C:37]1[CH:42]=[CH:41][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:39][CH:38]=1)=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]([C:30]([S:33]([CH3:36])(=[O:35])=[O:34])([CH3:32])[CH3:31])[CH:23]=[C:24]3[C:29]=2[N:28]=[CH:27][CH:26]=[CH:25]3)[CH:15]=1>CS(C)=O.O.C(OCC)(=O)C>[CH3:9][O:10][C:11]([C:12]1([C:37]2[CH:38]=[CH:39][C:40]([S:43]([CH3:46])(=[O:44])=[O:45])=[CH:41][CH:42]=2)[CH2:2][CH:13]1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]([C:30]([S:33]([CH3:36])(=[O:35])=[O:34])([CH3:32])[CH3:31])[CH:23]=[C:24]3[C:29]=2[N:28]=[CH:27][CH:26]=[CH:25]3)[CH:15]=1)=[O:47]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 69693966HCID 69693966, compound

Product 1

HCID 69694285HCID 69694285, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

To a suspension of trimethylsulfoxonium iodide (400 mg, 1.83 mmol) in DMSO (25 mL) at 0° C. was added NaH (60%, 73 mg, 1.83 mmol). After 30 min., 3-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester from Step 2 (688 mg, 1.22 mmol) was added and the resulting reaction mixture stirred for 18 h at 21° C., then diluted with water and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with toluene/acetone, 80:20) provided the 2-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-1-(4-methanesulfonyl-phenyl)-cyclopropanecarboxylic acid methyl ester compound.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with toluene/acetone, 80:20)

Sources & evidence

ORD record
ord-1c8ddb215fe848fe9764fac6b64429bd
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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