N-3-Bromopropylphthalimide → HCID 86691717, compound

HRID 1426904Notes

Reaction equation

HRID 1426904 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]3[N:14]=2)=[CH:5][CH:4]=[CH:3]1.[H-].[Li+].Br[CH2:30][CH2:31][CH2:32][N:33]1[C:41](=[O:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]1=[O:43]>CN(C=O)C>[O:43]=[C:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41](=[O:42])[N:33]1[CH2:32][CH2:31][CH2:30][O:1][C:2]1[N:7]=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]3[N:14]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 62714Lithium hydrideHCID 86691715HCID 86691715, compound

Product 1

HCID 86691717HCID 86691717, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of (R)-ethyl 5-(2-(6-oxo-1,6-dihydropyridin-2-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.091 g, 0.26 mmol) in DMF (2 mL) was added LiH (3.2 mg, 0.39 mmol) at 0° C. After stirring for 20 minutes, a solution of 2-(3-bromopropyl)isoindoline-1,3-dione (0.14 g, 0.52 mmol) in DMF (1 mL) was added, and the reaction was warmed up to ambient temperature and stirred for 17 hours. After cooling to 0° C., the reaction was quenched with ice-water (30 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated. The crude material was purified by silica column chromatography, eluting with 1.5% MeOH/DCM to yield the desired product (0.117 g, 84% yield). MS (apci) m/z=541.1 (M+H).

Workup

  1. stirringstirred for 17 hours
  2. temperatureAfter cooling to 0° C.
  3. customthe reaction was quenched with ice-water (30 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by silica column chromatography
  10. washeluting with 1.5% MeOH/DCM

Sources & evidence

ORD record
ord-4b464d2cb5594554a338af34dee56f08
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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