Sodium Iodide → HCID 68482717, compound

HRID 383275Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([C:22]5[CH:23]=[CH:24][C:25](=[O:28])[NH:26][CH:27]=5)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH2:30][CH3:31].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[CH2:30]([O:28][C:25]1[N:26]=[CH:27][C:22]([C:20]2[CH:19]=[CH:18][N:17]3[C:13]([C:11]4[CH:10]=[CH:9][N:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:12]=4)=[CH:14][N:15]=[C:16]3[CH:21]=2)=[CH:23][CH:24]=1)[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

5-[3-(2-Phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-1H-pyridin-2-one (Ex. 1.37) (1 eq, 0.096 mmol, 35 mg), iodoethane (1.5 eq, 0.144 mmol, 22.5 mg), sodium iodide (1.5 eq, 0.155 mmol, 21.5 mg) and cesium carbonate (2.99 eq, 0.287 mmol, 93.6 mg) are dissolved in DMF (2 ml) and heated at 60° C. for 16 h. The reaction mixture is diluted with CH2Cl2 and washed with Na2CO3. The organic phase is dried over MgSO4, filtered and evaporated to dryness. The reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 8/2 to yield 7-(6-ethoxy-pyridin-3-yl)-3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridine as a yellow solid; [M+H]+=393 and 1-ethyl-5-[3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-1H-pyridin-2-one as a yellow solid; [M+H]+=393

Workup

washwashed with Na2CO3
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
customevaporated to dryness
customThe reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 8/2

Sources & evidence

ORD record: ord-7a58e8ee385c4327ac589be9e10c9a34
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367662B2

Reaction notes

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