Ethanol → HCID 66671708, compound

HRID 2077565Notes

Reaction equation

HRID 2077565 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(O)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 95884-Fluorobenzenesulfonyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 66671708HCID 66671708, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a round bottom flask was added 5-bromopyridin-3-amine (0.80 g, 4.6 mmol, Matrix Scientific, Columbia S.C.), ethanol (15 mL) and 4-fluorobenzenesulfonyl chloride (2.2 g, 12 mmol, Fluka, St. Louis, Mo.). The mixture was allowed to stir at ambient temperature overnight. The mixture was diluted with CH2Cl2 and sat. NaHCO3, then the solution was extracted with CH2Cl2 (3×25 ml). The combined extracts were dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (10-30% EtOAc/CH2Cl2) afforded the title compound as an off-white crystalline solid (0.35 g, 23% yield). MS (ESI pos. ion) m/z: 333 (M+1). 1H NMR (400 MHz, MeOH-d4) δ ppm 8.35 (s, 1H), 8.22 (s, 1H), 7.83-7.89 (m, 2H), 7.76-7.81 (m, 1H), 7.25-7.32 (m, 2H).

Workup

  1. extractionthe solution was extracted with CH2Cl2 (3×25 ml)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (10-30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-b4e5368f30ad48dca7bfb3c10d41c3ea
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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