Triphenylphosphine → (S)-1-(4-benzyl-6-bromo-2-methyl-3,4-dihydropyrido[2,3-b]pyrazin-1(2H)-yl)ethanone

HRID 1485684Notes

Reaction equation

HRID 1485684 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:15]([N:22]([CH2:34][C@H:35](O)[CH3:36])[C:23]1[C:28]([NH:29][C:30](=[O:32])[CH3:31])=[CH:27][CH:26]=[C:25]([Br:33])[N:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:15]([N:22]1[CH2:34][C@H:35]([CH3:36])[N:29]([C:30](=[O:32])[CH3:31])[C:28]2[CH:27]=[CH:26][C:25]([Br:33])=[N:24][C:23]1=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 118080021(R)-N-(2-(benzyl(2-hydroxypropyl)amino)-6-bromopyridin-3-yl)acetamide

Product 1

HCID 118079717(S)-1-(4-benzyl-6-bromo-2-methyl-3,4-dihydropyrido[2,3-b]pyrazin-1(2H)-yl)ethanoneYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.763 mL, 3.93 mmol) was slowly added to a solution of (R)-N-(2-(benzyl(2-hydroxypropyl)amino)-6-bromopyridin-3-yl)acetamide (1.35 g, 3.57 mmol) and triphenylphosphine (1.030 g, 3.93 mmol) in THF (35.7 mL). A mild exotherm was observed. The reaction mixture stirred at room temperature for 30 minutes and was then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 10:1 dichloromethane-ethyl acetate) to afford (S)-1-(4-benzyl-6-bromo-2-methyl-3,4-dihydropyrido[2,3-b]pyrazine-1 (2H)-yl)ethanone (0.93 g, 72%). MS (ESI, pos. ion) m/z 360, 362 [M+1]+.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel (eluting with 10:1 dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-1d18cadc5a76494ebbcc33a9f7b13752
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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