Cesium carbonate → HCID 24803745, compound

HRID 2384927Notes

Reaction equation

HRID 2384927 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:32][C:17]3[C:18](=[O:31])[N:19]([C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([O:29][CH3:30])[CH:23]=4)[CH:20]=[CH:21][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1.[CH3:33][N:34]1[C:39](=[O:40])[CH2:38][O:37][CH2:36][C@H:35]1[CH2:41]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>CC#N>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:32][C:17]3[C:18](=[O:31])[N:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:41][C@@H:35]5[CH2:36][O:37][CH2:38][C:39](=[O:40])[N:34]5[CH3:33])=[C:24]([O:29][CH3:30])[CH:23]=4)[CH:20]=[CH:21][C:16]=3[CH:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 68951258HCID 68951258, compoundHCID 86629210HCID 86629210, compound

Product 1

HCID 24803745HCID 24803745, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add Cs2CO3 (339 mg, 1.04 mmol) to a slurry of 2-(4-chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-6H-thieno[2,3-c]pyridin-7-one, (Preparation 47) (200 mg, 0.522 mmol), in 10 mL CH3CN (10 mL). Stir 1 h and then add toluene-4-sulfonic acid (S)-4-methyl-5-oxo-morpholin-3-ylmethyl ester (172 mg, 0.57 mmol). Warm to reflux overnight. Cool to RT, pour into 1 M NaOH (100 mL) and extract with CH2Cl2 (3×100 mL). Wash the combined organic extracts with brine (100 mL). Purify via silica gel chromatography using 0-5-20% (2 N NH3 in MeOH)/CHCl3 to give 41 mg of product that is 86% pure. Recrystallize from CH2Cl2/hexanes to give 28 mg of the desired product in good purity. MS/ES m/z (35Cl) 511.0 [M+H]+.

Workup

  1. temperatureWarm
  2. temperatureto reflux overnight
  3. extractionextract with CH2Cl2 (3×100 mL)
  4. washWash the combined organic extracts with brine (100 mL)
  5. customPurify via silica gel chromatography

Sources & evidence

ORD record
ord-8ddae49313044825af3902cda5429f08
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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