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Sodium Iodide → HCID 68482717, compound

HRID 383275
Notes
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Reaction equation

HRID 383275 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 136337199HCID 136337199, compound

Product 1

HCID 68482717HCID 68482717, compound

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

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

  1. washwashed with Na2CO3
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes