Phthalimide → 2-((5-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 877777Notes

Reaction equation

HRID 877777 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:51]2[C:47](=[O:57])[C:48]3[C:49](=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:50]2=[O:52])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 579841692-((5-Bromopyridin-2-yl)methyl)isoindoline-1,3-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (5-bromopyridin-2-yl)methanol (1.2 g, 6.38 mmol), 1,1′-(azodicarbonyl)-dipiperidine (2.093 g, 8.30 mmol), triphenylphosphine (2.176 g, 8.30 mmol) and phthalimide (1.221 g, 8.30 mmol) in THF (60 mL) at rt was stirred over the weekend. The reaction mixture was filtered and the filtrate was concentrated to a yellow solid that was triturated with methanol. Filtration and drying afforded 2-((5-bromopyridin-2-yl)methyl)isoindoline-1,3-dione (1.295 g, 4.08 mmol, 64.0% yield) as a colorless crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=2.0 Hz, 1H), 8.03 (dd, J=8.4, 2.2 Hz, 1H), 7.90 (d, J=9.0 Hz, 4H), 7.44 (d, J=8.4 Hz, 1H), 4.89 (s, 2H). MS (ES+) m/z: 316.95, 318.96 (M+H); LC retention time: 2.297 min (analytical HPLC Method O).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to a yellow solid
  3. customthat was triturated with methanol
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-d3c06766ce3f4eda99ea063f4f3d0a15
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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