Water → 6-(6-Methoxy-3-pyridinyl)imidazo[1,2-a]pyridin-2-amine

HRID 555987Notes

Reaction equation

HRID 555987 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11]C(=O)C(F)(F)F)[N:10]=2)[CH:7]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH3:18][O:19][C:20]1[N:21]=[CH:22][C:23]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=3)[CH:7]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 12065953N-{6-bromoimidazo[1,2-a]pyridin-2-yl}-2,2,2-trifluoroacetamide2×

Product 1

HCID 669860156-(6-Methoxy-3-pyridinyl)imidazo[1,2-a]pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

N-(6-Bromo-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide (Intermediate A1, step 3) (0.84 g, 2.72 mmol), 2-methoxy-5-pyridineboronic acid (0.50 g, 3.27 mmol) and dry 1,4-dioxane (10 ml) are placed in a microwave vial and purged with Argon. Pd(PPh3)4 (0.16 g, 0.14 mmol) is added followed by a solution of Cs2CO3 in water (2.66 g, 8.16 mmol in 3 ml). The reaction mixture is heated using microwave radiation at 150° C. for 45 minutes and then left overnight at room temperature. The mixture is filtered through Celite® (filter agent) and washed through with EtOAc (100 ml). The organic filtrate is washed with NaHCO3 (50 ml) and brine (50 ml), dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with MeOH in DCM (1% increasing to 10%) affords the title compound. [MH+241.07].

Workup

  1. custompurged with Argon
  2. temperatureThe reaction mixture is heated
  3. customat 150° C.
  4. customfor 45 minutes
  5. filtrationThe mixture is filtered through Celite® (filter agent)
  6. washwashed through with EtOAc (100 ml)
  7. washThe organic filtrate is washed with NaHCO3 (50 ml) and brine (50 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by flash chromatography on silica eluting with MeOH in DCM (1% increasing to 10%)

Sources & evidence

ORD record
ord-b286b40771ef48668e1d3353bbd08baf
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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