Sodium hydride → HCID 86701851, compound

HRID 1844090Notes

Reaction equation

HRID 1844090 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH:3]2[CH2:7][C:8]3[C:13]([CH:2]12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[Na+].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=1>C1(C)C=CC=CC=1>[O:6]=[C:5]1[N:1]([C:17]2[N:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=2)[CH:2]2[C:13]3[C:8]([CH2:7][CH:3]2[CH2:4]1)=[CH:9][CH:10]=[CH:11][CH:12]=3

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 67975592HCID 67975592, compound

Product 1

HCID 86701851HCID 86701851, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one (1 g, 5.77 mmol) in toluene (15 ml) was added sodium hydride (0.254 g, 6.35 mmol) at 0° C. The batch was warmed to room temperature and 2-chloro-5-cyanopyridine (0.824 g, 5.77 mmol) was added. The batch was stirred at 95° C. for 2 h. After cooling, the batch was added to ice water and extracted with ethyl acetate (2×). The combined organic phases were concentrated and the residue was purified by column chromatography (hexane/ethyl acetate 7/3) to give 6-(2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrol-1-yl)pyridine-3-carbonitrile F20 (1.00 g, 63%). LCMS (method A) 1.68 min; ES+: 276 (M+H+).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×)
  3. concentrationThe combined organic phases were concentrated
  4. customthe residue was purified by column chromatography (hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-66147c7c56a44b248cb423974a106c77
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

Loading…