Potassium Carbonate → HCID 66759397, compound

HRID 389459Notes

Reaction equation

HRID 389459 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]3)[CH:13]=2)O1.[Cl:24][C:25]1[O:35][C:28]2=[C:29]([NH2:34])[N:30]=[CH:31][C:32](I)=[C:27]2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O>[NH2:34][C:29]1[N:30]=[CH:31][C:32]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:15][CH2:16][N:17]([C:20](=[O:22])[CH3:21])[CH2:18][CH2:19]3)[CH:13]=2)=[C:27]2[CH:26]=[C:25]([Cl:24])[O:35][C:28]=12

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 593927031-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidin-1-yl)ethanoneHCID 667601342-Chloro-4-iodofuro[2,3-c]pyridin-7-amine

Product 1

HCID 66759397HCID 66759397, compoundYield 86.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (422 mg, 1.32 mmol) and 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (354 mg, 1.20 mmol) in 1,4-dioxane (8.06 mL) and H2O (2 mL) was charged with potassium carbonate (250 mg, 0.0018 mol) and (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride (9 mg, 0.01 mmol) under an atmosphere of nitrogen. The mixture was heated in a microwave at 100° C. for 40 min. The reaction mixture was dissolved in EtOAc and then washed with brine (2×). The aqueous layer was back-extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to a solid. The product was then purified by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc) to afford 374 mg (86%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.05 (s, 1 H), 7.89 (s, 1 H), 7.83 (s, 1 H), 7.05 (s, 1 H), 4.67 (dd, J=13.52, 1.89 Hz, 1 H), 4.50 (tt, J=11.46, 4.20 Hz, 1 H), 4.08 (d, J=13.89 Hz, 1 H), 3.32-3.37 (m, 1 H), 2.79-2.91 (m, 1 H), 1.91-2.24 (m, 7 H). MS (ESI): 362.11 [M+H]+; HPLC tR=0.88 min (TOF: polar—3 min).

Workup

  1. washwashed with brine (2×)
  2. extractionThe aqueous layer was back-extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a solid
  6. customThe product was then purified by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-9c92471002304b8db61a4cead19f91fd
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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