Thiophenol → HCID 67421842, compound

HRID 1784225Notes

Reaction equation

HRID 1784225 reaction equation
C[C:2]1[C:3]([CH:8]2[CH:13](C)[CH2:12][CH2:11][CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:9]2[CH2:21][CH:22]2[CH2:25][N:24](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:23]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[NH:24]1[CH2:23][CH:22]([CH2:21][N:9]2[CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:12][CH2:13][CH:8]2[C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 67422163HCID 67422163, compound

Product 1

HCID 67421842HCID 67421842, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3,3′-dimethyl-1′-[1-(2-nitro-benzenesulfonyl)-azetidin-3-ylmethyl]-1′,2′,3′4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (168 mg, 0.322 mmol), thiophenol (0.3 mL), K2CO3 (500 mg) in CH3CN (5 mL) were stirred at room temperature for 17 hours. The volatiles were removed under reduced pressure and saturated NaHCO3 (15 mL) was added and the mixture was extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude material was subjected to column chromatography on silica gel (10:1:0.1 CH2Cl2:CH3OH:NH4OH; then 10:1:0.5) to provide 1′-azetidin-3-ylmethyl-1′,2′,3′4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (74 mg, 80% pure by LC/MS).

Workup

  1. customThe volatiles were removed under reduced pressure and saturated NaHCO3 (15 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-66f1a9641cb44e7daa1ddf8302288fe0
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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