Potassium Iodide → HCID 69639853, compound

HRID 1245409Notes

Reaction equation

HRID 1245409 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:11]1)=[O:4].Cl[CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([CH3:34])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:17][CH:16]=2)[CH2:11]1)=[O:4]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 115357194-(Chloromethyl)-2-methylquinolineHCID 136336352HCID 136336352, compound

Product 1

HCID 69639853HCID 69639853, compoundYield 47%

Conditions

Temperature
50 °C

Procedure

The product from step 28a (0.31 g, 1.1 mmol) was combined with 4-chloromethyl-2-methylquinoline (0.20 g, 1.0 mmol), potassium carbonate (0.22 g, 1.6 mmol) and potassium iodide (0.05 g, 0.3 mmol) in acetontrile (5 mL) under a nitrogen atmosphere and heated to 50° C. for 18 h. The reaction was filtered, concentrated, and purified by FCC on silica gel eluting ethyl an acetate:hexanes gradient to give cis-2-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-cyclopentanecarboxylic acid methyl ester (0.19 g, 47%) as an oil. MS found: (M+H)+=445.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified by FCC on silica gel
  4. washeluting ethyl an acetate

Sources & evidence

ORD record
ord-dde6edae184440d5b50b040fbf2fe037
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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