HCID 58547443, compound → HCID 58547620, compound

HRID 1850253Notes

Reaction equation

HRID 1850253 reaction equation
F[C:2]1[C:7]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:15]([O:14][C:12]([N:10]1[CH2:11][CH:8]([C:7]2[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 2

HCID 58547443HCID 58547443, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 58547620HCID 58547620, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9834912Nickel(II) acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-fluoro-pyridin-3-yl)-azetidine-1-carboxylic acid tert-butyl ester (25) (200 mg, 0.80 mmol), Ni(acac)2 (20 mg, 0.08 mmol), DPPF (32 mg, 0.08 mmol) in THF (10 mL) was added PhMgBr (1 M, 0.8 mL, 0.80 mmol). The resulting mixture was heated to reflux overnight under N2 atmosphere. TLC showed that the staring material was consumed completely. The solution was filtered and the filtrate was concentrated to give the residue, The crude compound was purified by column chromatography on silica gel to give the product 3compound (27) (180 mg, yield 78%) as solid. ESI-MS (M+1): 311 calc. for C19H22N2O2 310.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight under N2 atmosphere
  3. customwas consumed completely
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give the residue
  7. customThe crude compound was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9d8bc19c356e442c8d03a711baa0bd53
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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