Pyridine → HCID 68891681, compound

HRID 2220221Notes

Reaction equation

HRID 2220221 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][NH:11][C:10]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][N:11]([S:26]([CH3:25])(=[O:28])=[O:27])[C:10]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68893382HCID 68893382, compound

Product 1

HCID 68891681HCID 68891681, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 9-Bromo-2-chloro-5,6-dihydro-dibenzo[b,f]azocine (30 mg, 0.09 mmol) (prepared in a manner analogous to that described for Example 1F) in dichloroethane was treated with pyridine (0.02 mL, 0.27 mmol) and methanesulfonyl chloride (0.009 mL, 0.12 mmol). The reaction mixture was stirred at room temperature for two hours then concentrated, diluted with MeOH and filtered. The crude product was purified by preparative reversed-phase HPLC to afford Example 330A (16 mg). HPLC Rt=3.66 min. m/z=398 (M+H+)

Workup

  1. concentrationthen concentrated
  2. additiondiluted with MeOH
  3. filtrationfiltered
  4. customThe crude product was purified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-8c432488766245c88ce5399ed081dad4
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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