Pyridine-3-sulfonyl chloride → HCID 10292214, compound

HRID 1173135Notes

Reaction equation

HRID 1173135 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[Br:12].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:14]=1>N1C=CC=CC=1.[Cl-].[Na+].O>[Br:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([NH:1][S:19]([C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)(=[O:21])=[O:20])=[CH:11]2

Participants

5

Reactant 2

HCID 3164136Pyridine-3-sulfonyl chlorideHCID 226741618-Bromoquinolin-3-amine

Product 1

HCID 10292214HCID 10292214, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Amino-8-bromoquinoline (300 mg, Production Example 5b) was dissolved in pyridine (5 ml), to which was then added 3-pyridinesulfonyl chloride (254 mg), followed by stirring at room temperature for 30 minutes. After the reaction was completed, the reaction solution was poured into brine and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated. The resulting crude crystals were washed with ethyl acetate and IPA, to give the title compound (270 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. washThe resulting crude crystals were washed with ethyl acetate and IPA

Sources & evidence

ORD record
ord-5be52e612ed242be80a0efd9a6dcaae2
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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