Potassium Carbonate → HCID 66759894, compound

HRID 389490Notes

Reaction equation

HRID 389490 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)[CH:25]=2)=[C:15]2[C:19]([Cl:20])=[CH:18][O:17][C:16]=12.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)[CH:25]=2)=[C:15]2[C:19]([Cl:20])=[C:18]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:17][C:16]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 66760546HCID 66760546, compound

Product 1

HCID 66759894HCID 66759894, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of phenylboronic acid (35.0 mg, 287 μmol), tert-butyl 4-[4-(7-amino-3-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (65 mg, 144 μmol), (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride (10.5 mg, 14.4 μmol), potassium carbonate (29.8 mg, 216 μmol) in 1,4-dioxane (785 μL) and H2O (259 μL) was evacuated and filled with argon three times. The mixture was irradiated in a microwave reactor at 100° C. for 40 min. The reaction mixture was partitioned between EtOAc and brine/water and separated. The aqueous layer was extracted with EtOAc (3×) and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (60 to 100% EtOAc:hexanes) to afford tert-butyl 4-[4-(7-amino-3-chloro-2-phenylfuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate. MS (ESI): 494.16 [M+H]+; HPLC tR=3.11 min.

Workup

  1. additionfilled with argon three times
  2. customThe mixture was irradiated in a microwave reactor at 100° C. for 40 min
  3. customThe reaction mixture was partitioned between EtOAc and brine/water
  4. customseparated
  5. extractionThe aqueous layer was extracted with EtOAc (3×)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (60 to 100% EtOAc:hexanes)

Sources & evidence

ORD record
ord-d3548e2111004b8c875f0550d86d83d7
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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