Potassium Carbonate → 4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenylamine

HRID 1446662Notes

Reaction equation

HRID 1446662 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[CH:9][N:10]=[C:4]2[CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridine

Product 1

HCID 685394114-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenylamineYield 100%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

To a round bottomed flask add 7-chloro-3-iodo-imidazo[1,2-a]pyridine (3.0 g, 0.011 mol), add 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.6 g, 1.1 equiv.), potassium carbonate (4.5 g, 3 equiv.), dioxane (40 mL), and water (20 mL). Deoxygenate this mixture thoroughly with N2 then add dichlorobis(triphenylphosphine)palladium (II) (0.23 g, 0.03 equiv.) and reflux the reaction overnight under N2. Concentrate the reaction to dryness and slurry in DCM. Filter this slurry thru Celite® and wash with DCM. Concentrate the filtrate then purify by silica plug (EtOAc to 5% MeOH: DCM to 10% MeOH: DCM) to give a pale grey solid (2.6 g, 100%). MS (ES), m/z 244 (M+1).

Workup

  1. customDeoxygenate this mixture thoroughly with N2
  2. customthe reaction overnight under N2
  3. concentrationConcentrate
  4. customthe reaction to dryness and slurry in DCM
  5. filtrationFilter this slurry thru Celite®
  6. washwash with DCM
  7. concentrationConcentrate the filtrate
  8. customthen purify by silica plug (EtOAc to 5% MeOH: DCM to 10% MeOH: DCM)

Sources & evidence

ORD record
ord-6b0cbc677db84ef98bfb4419ea8b46ae
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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