Picolyl chloride hydrochloride → HCID 12094708, compound

HRID 1432228Notes

Reaction equation

HRID 1432228 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:18][C:9]2=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1.[H-].[Na+].Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:18]([CH2:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=2)[C:9]2=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1

Participants

6

Reactant 4

HCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 15486854HCID 15486854, compound

Product 1

HCID 12094708HCID 12094708, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-furanyl)-5-methanesulfonyl-1H-pyrrolo [2,3-b]pyridine (140 mg) in N,N-dimethylformamide (5 ml), 60% sodium hydride (53.6 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred for 30 minutes. Subsequently, 2-picolyl chloride hydrochloride (105 mg) was added thereto, followed by stirring at 15 to 30° C. for 15 hours. The reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with toluene, washed with a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (ethyl acetate:n-hexane 1:1). The resulting crystal was further recrystallized from methanol to obtain 69.3 mg (37%) of the desired product as a pale yellow needle-like crystal.

Workup

  1. stirringby stirring at 15 to 30° C. for 15 hours
  2. extractionextracted with toluene
  3. washwashed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated
  8. customThe resulting crystal was further recrystallized from methanol

Sources & evidence

ORD record
ord-a5ade6f4330546c6b726fee136f2cf27
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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