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

HRID 1446672Notes

Reaction equation

HRID 1446672 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:20][C:19]=1[NH2:33].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[Cl:17][C:18]1[CH:23]=[C:22]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]4[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=4)=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:21]=[CH:20][C:19]=1[NH2:33]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 441187962-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 685421433-Iodo-7-pyridin-4-yl-imidazo[1,2-a]pyridine

Product 1

HCID 685472852-Chloro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenylamineYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 3-iodo-7-pyridin-4-yl-imidazo[1,2-a]pyridine (2.18 g, 6.8 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (crude material from previous step, excess), potassium carbonate (2.8 g, 3 equiv.), dioxane (30 mL), and water (15 mL). De-gas thoroughly with nitrogen then add dichloro-bis(triphenylphosphine) palladium (II) (0.143 g, 3 mol %). Heat reaction at 80° C. overnight. Concentrate to dryness then slurry in DCM and filter via Celite®, washing with DCM. Concentrate filtrate then purify by silica plug (Hexanes→1:1 Hexanes:Ethyl Acetate→2.5% Methanol:DCM→5% Methanol:DCM) to give an orange-yellow solid (1.42 g, 46%). MS (ES), m/z 321.1 (M+1).

Workup

  1. customDe-gas thoroughly with nitrogen
  2. temperatureHeat
  3. customreaction at 80° C. overnight
  4. concentrationConcentrate to dryness
  5. filtrationfilter via Celite®
  6. washwashing with DCM
  7. customConcentrate filtrate then purify by silica plug (Hexanes→1:1 Hexanes:Ethyl Acetate→2.5% Methanol:DCM→5% Methanol:DCM)

Sources & evidence

ORD record
ord-d8f539760807457e9a00c4e371281c2f
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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