Potassium Carbonate → HCID 59293415, compound

HRID 2387502Notes

Reaction equation

HRID 2387502 reaction equation
FC(F)(F)S([O:6][C:7]1[CH:12]=[CH:11][N:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][CH:23]([O:26][CH3:27])[O:24][CH3:25])[N:17]=[CH:16]3)[C:9](=[O:28])[CH:8]=1)(=O)=O.[C:31]1([CH:37]=[CH:38]B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:7][OH:6].[NH3:10].[CH3:27][O:26][CH:23]([O:24][CH3:25])[CH2:22][N:18]1[C:19]2[C:15](=[CH:14][C:13]([N:10]3[CH:11]=[CH:12][C:7](/[CH:38]=[CH:37]/[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:8][C:9]3=[O:28])=[CH:21][CH:20]=2)[CH:16]=[N:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343812-Phenylvinylboronic acidHCID 59293402HCID 59293402, compound

Product 2

HCID 21705897Ammonia methanolYield 10%HCID 59293415HCID 59293415, compoundYield 174.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

1-(1-(2,2-Dimethoxyethyl)-1H-indazol-5-yl)-2-oxo-1,2-dihydropyridin-4-yl trifluoromethanesulfonate (2.66 mg, 5.95 mmol), phenylvinylboronic acid (2.23 g, 14.8 mmol), K2CO3 (2.05 g, 14.8 mmol) and PdCl2dppf (500 mg, 0.595 mmol) were stirred in DMSO (15 mL) under vacuum for 30 min. The flask was flushed with nitrogen and the mixture was heated at 80° C. for 1 h. Upon cooling, the mixture was diluted with methylene chloride, washed with 5% lithium chloride solution (5×), dried, concentrated, and the residue was purified by column chromatography (120 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 10% methanol/ammonia mixture (10:1) over 60 min at 40 mL/min) to provide the title compound (2.08 g, 87%): 1H NMR (500 MHz, CD3OD) 8.06 (s, 1H), 7.72 (d, J=17 Hz, 1H), 7.60-7.54 (m, 3H), 7.45-7.34 (m, 5H), 7.23 (d, J=16.6 Hz, 1H), 6.95 (d, J=16.6 Hz, 1H), 6.68 (d, J=1.5 Hz, 1H), 6.54-6.51 (dd, J=7.3, 1.8 Hz, 1H), 4.78 (t, J=5.3 Hz, 1H), 4.51 (t, J=5.3 Hz, 2H), 3.38 (s, 6H).

Workup

  1. customThe flask was flushed with nitrogen
  2. temperatureUpon cooling
  3. additionthe mixture was diluted with methylene chloride
  4. washwashed with 5% lithium chloride solution (5×)
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography (120 g ISCO column
  8. washeluting with methylene chloride

Sources & evidence

ORD record
ord-3bcd7d5cb5bb40d29a3903f91fbcd130
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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