Sodium Iodide → HCID 5329351, compound

HRID 1245484Notes

Reaction equation

[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=4)=[CH:15][C:10]3=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][N:19]([CH2:32][CH2:33][CH2:34][N:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)[C:18](=[O:22])[CH:17]=4)=[CH:15][C:10]3=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(3-phenylimidazo[1,2-a]pyridin-7-yl)pyridin-2(1H)-one (0.050 g, 0.173 mmol) in 1.0 mL of anhydrous DMF was added sodium iodide (0.038 g, 0.260 mmol), cesium carbonate (0.140 g, 0.430 mmol), and 1-(3-chloropropyl)piperidine (0.0420 g, 0.25 mmol). Reaction was refluxed at 40° C. overnight. Poured reaction into saturated sodium bicarbonate solution and extracted with methylene chloride. Dried organic over sodium sulfate. Removed solvent under reduced pressure. Purified by silica chromatography (10% MeOH/CH2Cl2). 1H NMR (CDCl3) δ 8.40 (d, 1H, J=6.59 Hz), 7.92 (s, 1H), 7.78 (s, 1H), 7.62–7.52 (m, 4H), 7.50 (d, 1H, J=7.09 Hz), 7.45 (t, 1H, J=7.33 Hz), 7.06 (dd, 1H, J=7.08, 1.71 Hz), 6.84 (s, 1H), 6.50 (dd, 1H, J=7.08, 2.20 Hz), 4.08 (t, 2H, J=6.84 Hz), 2.40 (bs, 2H), 2.02 (bs, 2H), 1.62 (bs, 8H), 1.46 (bs, 2H). HRMS m/z (M+1) Calc: 413.2, found: 413.3.

Workup

customReaction
additionPoured
extractionextracted with methylene chloride
customPurified by silica chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-f61f3313c55642479fdf371c3892408d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125888B2

Reaction notes

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