o-Toluenesulfonyl chloride → HCID 86653305, compound

HRID 1695748Notes

Reaction equation

HRID 1695748 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:10])(=[O:19])=[O:18])[C:3]([Cl:9])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 86653305HCID 86653305, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Amino-5-bromo-2-chloropyridine (767 mg) in dry pyridine (8 ml) was treated with 2-methylbenzenesulfonyl chloride (641 μl) then stirred at RT overnight. The reaction was purified by prep-HPLC. Desired fractions were combined, diluted with saturated sodium bicarbonate (aq) and brine and extracted into EtOAc. The solvent was dried over sodium sulfate and evaporated to give title compound (500 mg).

Workup

  1. customThe reaction was purified by prep-HPLC
  2. additiondiluted with saturated sodium bicarbonate (aq) and brine
  3. extractionextracted into EtOAc
  4. dry with materialThe solvent was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f122f18d83434d76a85b3007432f2bf1
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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