m-Chloroperbenzoic acid → 3-Bromo-2-(methoxycarbonylamino)-6-phenylsulfinyl imidazo [1,2-a] pyridine

HRID 1413434Notes

Reaction equation

HRID 1413434 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[C:8]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:18][C:19]([O:21][CH3:22])=[O:20].ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[Br:1][C:2]1[N:6]2[CH:7]=[C:8]([S:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:31])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:18][C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 544631513-Bromo-2(methoxycarbonylamino)-6(phenylthio) imidazo [1,2-a] pyridine

Product 1

HCID 538100123-Bromo-2-(methoxycarbonylamino)-6-phenylsulfinyl imidazo [1,2-a] pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, one may treat a suspension of 3-bromo-2(methoxycarbonylamino)-6(phenylthio) imidazo [1,2-a] pyridine (1.0 gm. 2.64 mmoles) in 100 ml. of dichloromethane with 85% metachloroperbenzoic acid (464 mg., 2.64 mmoles). After 1 hour at room temperature, the solution is washed with aqueous saturated sodium bicarbonate solution, and with water. After drying the solvent is removed in vacuo and the residue is chromatographed over silica gel to yield 3-bromo-2-(methoxycarbonylamino)-6-phenylsulfinyl imidazo [1,2-a] pyridine m.p. 150°-152° C.

Workup

  1. additionAlternatively, one may treat
  2. washthe solution is washed with aqueous saturated sodium bicarbonate solution
  3. customAfter drying the solvent
  4. customis removed in vacuo
  5. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-9b47318919064db39001fc0a3072aa2a
Source dataset
uspto-grants-1981_02
Patent number
US04250174

Reaction notes

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