Ethanol → HCID 66671708, compound

HRID 1162442Notes

Reaction equation

HRID 1162442 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-bottomed 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 (Sigma-Aldrich) Buchs, Switzerland). The mixture was allowed to stir at ambient temperature overnight. The mixture was diluted with CH2Cl2 and sat. NaHCO3 and 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 N-(5-bromopyridin-3-yl)-4-fluorobenzenesulfonamide 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-de2bdd697181426390da3883305897ee
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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