5-Fluoro-2-methylbenzenesulphonyl chloride → N-(5-Bromo-2-chloro-3-pyridinyl)-5-fluoro-2-methylbenzenesulfonamide

HRID 1695749Notes

Reaction equation

HRID 1695749 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([S:17](Cl)(=[O:19])=[O:18])[CH:16]=1>N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:17]([C:15]2[CH:16]=[C:11]([F:10])[CH:12]=[CH:13][C:14]=2[CH3:21])(=[O:18])=[O:19])[C:3]([Cl:9])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 86653306N-(5-Bromo-2-chloro-3-pyridinyl)-5-fluoro-2-methylbenzenesulfonamideYield 59.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Amino-5-bromo-2-chloropyridine (797 mg) in dry pyridine (10 ml) was treated with 5-fluoro-2-methylbenzenesulfonyl chloride (962 mg) then stirred at RT over the weekend. The reaction was purified by prep-HPLC. Desired fractions were concentrated under reduced pressure, diluted with saturated sodium bicarbonate (aq) and brine and extracted into DCM. The solvent was dried over magnesium sulfate, filtered then evaporated to give title compound (865 mg).

Workup

  1. customThe reaction was purified by prep-HPLC
  2. concentrationDesired fractions were concentrated under reduced pressure
  3. additiondiluted with saturated sodium bicarbonate (aq) and brine
  4. extractionextracted into DCM
  5. dry with materialThe solvent was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthen evaporated

Sources & evidence

ORD record
ord-ef37bac9dc5548a691ae03e1062d2d1d
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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