Potassium Carbonate → HCID 57813261, compound

HRID 564497Notes

Reaction equation

HRID 564497 reaction equation
BrC1C=C(C[N:11]([CH2:23][C:24]2[C:25]([NH:37][CH:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[C:26]3[CH:34]=[N:33][N:32]([CH2:35][CH3:36])[C:27]3=[N:28][C:29]=2[CH2:30][CH3:31])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([NH2:22])=[O:21])[CH:15]=2)=[O:13])C=CC=1OC.[CH:44]([C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1)=[O:45].[C:55](=[O:58])([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=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>[CH2:35]([N:32]1[C:27]2=[N:28][C:29]([CH2:30][CH3:31])=[C:24]([CH2:23][NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([NH:22][CH2:12][C:14]4[CH:15]=[C:16]([C:48]5[CH:49]=[CH:50][CH:51]=[C:46]([CH:44]=[O:45])[CH:47]=5)[C:17]([O:58][CH3:55])=[CH:18][CH:19]=4)=[O:21])[CH:15]=3)=[O:13])[C:25]([NH:37][CH:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)=[C:26]2[CH:34]=[N:33]1)[CH3:36]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27343563-Formylphenylboronic acidHCID 67005891HCID 67005891, compound

Product 1

HCID 57813261HCID 57813261, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-{[3-Bromo-4-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide (0.64 g, 0.99 mmol), (3-formylphenyl)boronic acid (0.193 g, 1.29 mmol), potassium carbonate (0.41 g, 2.97 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.05 mmol) were combined in dioxane (6 mL) and water (2 mL). The mixture was microwaved at 150° C. for 30 min. The reaction mixture was diluted with EtOAc and washed 3× with H2O. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified using CombiFlash on a 40 g column eluted with 0-10% MeOH/CH2Cl2 to give the title compound as a white solid. LC-MS m/z 675.1 (M+H)+, 1.85 min (ret time); mp 118-121° C.; analytical HPLC shows 100% purity, (ret time 13.204 min).

Workup

  1. customThe mixture was microwaved at 150° C. for 30 min
  2. washwashed 3× with H2O
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. washeluted with 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2bc11a2d420145f79da98b46d38f053c
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

Loading…