Sodium Carbonate → HCID 57813366, compound

HRID 564543Notes

Reaction equation

HRID 564543 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=1C#N.[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.[Na+].[Na+]>O1CCOCC1.O>[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)[CH:17]=[CH:18][C:19]=4[O:58][CH3:55])=[O:21])[CH:15]=3)=[O:13])[C:25]([NH:37][CH:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[C:26]2[CH:34]=[N:33]1)[CH3:36]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 67005908HCID 67005908, compound

Product 1

HCID 57813366HCID 57813366, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-[(3-bromo-4-cyanophenyl)methyl]-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide (0.779 g, 0.00120 mol) in dioxane (9 mL) with (3-formylphenyl)boronic acid (234.7 mg, 0.001565 mol) was treated with a solution of Na2CO3 (382.8 mg, 0.00361 mol) in H2O (3 mL). The mixture was purged with N2 for 10 min, then Tetrakistriphenylphosphine palladium (0) (69 mg, 0.00060 mol) was added. The mixture was microwaved at 150° C. for 30 min. The reaction was quenched with H2O, then the mixture was extracted with EtOAc (2×). The combined organic extracts were washed with H2O, then sat. aq. NaCl, dried (Na2SO4) and concentrated giving a residue which was purified on a Chomatotrom™ Plate (2000μ) silica gel [DCM-MeOH, 0-6%] to afford the title compound (438 mg). However, there was loss of Br during the reaction and the des-bromo compound did not separate under the chromatographic conditions and the product 70% pure, with effectively 306 mg (38%) desired product obtained. LC-MS m/z 675.5 (M+H)+.

Workup

  1. customThe mixture was purged with N2 for 10 min
  2. customThe mixture was microwaved at 150° C. for 30 min
  3. customThe reaction was quenched with H2O
  4. extractionthe mixture was extracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with H2O
  6. dry with materialsat. aq. NaCl, dried (Na2SO4)
  7. concentrationconcentrated
  8. customgiving a residue which
  9. customwas purified on a Chomatotrom™ Plate (2000μ) silica gel [DCM-MeOH, 0-6%]

Sources & evidence

ORD record
ord-899ad51a35fa40128bc392c146e2d9fb
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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