Potassium Carbonate → HCID 66760120, compound

HRID 389504Notes

Reaction equation

HRID 389504 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH:15]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:13]=[N:12]2)[CH2:7][CH2:6]1.I[C:26]1[CH:31]=[N:30][C:29]([NH2:32])=[C:28]2[O:33][C:34]([C:36]3[CH:45]=[CH:44][CH:43]=[C:42]4[C:37]=3[CH:38]=[CH:39][N:40]=[CH:41]4)=[CH:35][C:27]=12.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:41]1[C:42]2[C:37](=[C:36]([C:34]3[O:33][C:28]4=[C:29]([NH2:32])[N:30]=[CH:31][C:26]([C:14]5[CH:13]=[N:12][N:11]([CH:8]6[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:10][CH2:9]6)[CH:15]=5)=[C:27]4[CH:35]=3)[CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:39][N:40]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 667594744-Iodo-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amineHCID 66760559HCID 66760559, compound

Product 1

HCID 66760120HCID 66760120, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A vial was charged with 1-(2-methoxyethyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine (32.4 mg, 96.8 μmol) and 4-iodo-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amine (25.0 mg, 64.6 μmol) in 1,4-dioxane (0.43 mL) and H2O (0.1 mL), potassium carbonate (13 mg, 97.0 μmol) and (1,1′-bis(diphenylphosphino)ferrocene) palladium dichloride (5 mg, 6 μmol) was evacuated and filled with argon three times. The mixture was heated 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. Purification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc) afforded 1.9 mg (6%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 9.33 (s, 1 H), 8.57 (d, J=6.06 Hz, 1 H), 8.49 (d, J=6.06 Hz, 1 H), 8.34 (dd, J=7.33, 1.26 Hz, 1 H), 8.23 (d, J=8.34 Hz, 1 H), 8.13 (s, 1 H), 7.92 (d, J=9.09 Hz, 2 H), 7.82 (t, J=7.71 Hz, 1 H), 7.49 (s, 1 H), 4.25 (dt, J=15.54, 7.89 Hz, 1 H), 3.58 (t, J=5.56 Hz, 2 H), 3.37 (s, 3 H), 3.15 (d, J=12.13 Hz, 2 H), 2.66 (t, J=5.56 Hz, 2 H), 2.26-2.35 (m, 2 H), 2.13-2.20 (m, 4 H); MS (ESI): 469.23 [M+H]+; HPLC tR=0.77 min (TOF: polar—3 min).

Workup

  1. customwas evacuated
  2. additionfilled with argon three times
  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. customPurification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-5632928f091a425fa40dabea4c6cce9a
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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