Cesium carbonate → HCID 22504877, compound

HRID 1814178Notes

Reaction equation

HRID 1814178 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C[O:8][C:9](=[O:21])[CH2:10][C:11]1[C:12]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[C:13]=2[S:14][CH:15]=1.Cl[CH2:23][C:24]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[O:26][N:25]=1>C(#N)C.ClCCl>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:27]2[O:26][N:25]=[C:24]([CH2:23][O:20][C:16]3[C:13]4[S:14][CH:15]=[C:11]([CH2:10][C:9]([OH:8])=[O:21])[C:12]=4[CH:19]=[CH:18][CH:17]=3)[CH:28]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 14811003-(Chloromethyl)-5-(4-chlorophenyl)-1,2-oxazoleHCID 20770870HCID 20770870, compound

Product 1

HCID 22504877HCID 22504877, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Cesium carbonate (0.31 g, 90 mmol) was added to a stirred solution of compound 77B from the preceding step (0.14 g, 0.63 mmol) and commercially available 3-chloromethyl-5-(4-chloro-phenyl)-isoxazole (0.14 g, 0.63 mmol) in 15-20 mL of acetonitrile at room temp. After 20 hours the mixture was stripped of solvent in vacuo. The residue was dissolved in dichloromethane and filtered through a short column of Celite® over silica gel, eluting with several column volumes of solvent. The filtrate was stripped of solvent in vacuo, and the residue recrystallized from DMF to afford 0.1 g (38% yield) of the title compound as a snow-white solid; mp 155-156° C. Calc for C21H16ClNO4S: C, 60.94; H, 3.90; N, 3.38. found: C, 60.67; H, 3.72; N, 3.41. Step 4. Preparation of {7-[5-(4-Chloro-phenyl)-isoxazol-3-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid (Compound 77D)

Workup

  1. filtrationfiltered through a short column of Celite® over silica gel
  2. washeluting with several column volumes of solvent
  3. customthe residue recrystallized from DMF

Sources & evidence

ORD record
ord-c08dadcdb2164f2fb6d8a3b0f0d150dd
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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