4-Bromopyridine → HCID 68567233, compound

HRID 1867609Notes

Reaction equation

HRID 1867609 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:13]([O:17][C:18]([N:20]([CH2:37]/[CH:38]=[N:39]/[S:40]([C:42]([CH3:45])([CH3:44])[CH3:43])=[O:41])[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CCOCC>[C:13]([O:17][C:18]([N:20]([CH2:37][CH:38]([NH:39][S:40]([C:42]([CH3:45])([CH3:44])[CH3:43])=[O:41])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28])[CH2:23][CH2:22]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 142684-BromopyridineHCID 87498688HCID 87498688, compoundHCID 178418339Butyllithium

Product 1

HCID 68567233HCID 68567233, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

4-Bromopyridine (360 mg, 2.28 mmol) in ether (5 mL) was added dropwise to a solution of n-butyllithium (2.5 M, 1.0 μL, 2.5 mmol) in ether (15 mL) at −78° C. After 30 min, benzyl 4-((tert-butoxycarbonyl) {(2E)-2-[(tert-butylsulfinyl)imino]ethyl}amino)piperidine-1-carboxylate (364 mg, 0.759 mmol) in ether (6 mL) was added to the mixture. After 1 h, the reaction was warmed to ambient temperature, quenched with saturated ammonium chloride solution (2 mL), and partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography chromatography (75%-100% ethyl acetate/hexanes) to give the title compound (230 mg). MS 559.2 (M+1)

Workup

  1. waitAfter 1 h
  2. customquenched with saturated ammonium chloride solution (2 mL)
  3. custompartitioned between dichloromethane and saturated sodium bicarbonate solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography chromatography (75%-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-942b698b5e284beea331db6cc0c6bf60
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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