Potassium Carbonate → HCID 53311138, compound

HRID 571015Notes

Reaction equation

HRID 571015 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[C:8]1[C:9]([NH2:24])=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[CH:13]=1.[NH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)=[O:27]>O1CCOCC1.CN(C=O)C>[NH2:24][C:9]1[C:8]([C:31]2[CH:32]=[CH:33][C:28]([C:26]([NH2:25])=[O:27])=[CH:29][CH:30]=2)=[CH:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27378114-Aminocarbonylphenylboronic acidHCID 53311903HCID 53311903, compound

Product 1

HCID 53311138HCID 53311138, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Aqueous K2CO3 solution (1 M, 0.4 mL) was added to a suspension of 3-bromo-5-[4-(methylsulfonyl)phenyl]pyridin-2-amine obtained as described above (0.15 g, 0.46 mmol), 4-aminocarbonylphenylboronic acid (0.120 g, 0.51 mmol) and Pd[(PPh)3]4 (0.016 g, 0.02 mmol) in dioxane (5 mL) and DMF (2 mL) under N2. The reaction mixture was stirred at 120 ° C. for 14 h, poured onto H2O (10 mL) and extracted with MeOH/CHCl3 (1:4) (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (5% MeOH/EtOAc) to yield the desired product (0.26 g, 56%). 1H NMR (400 MHz, DMSO-d6): δ 8.45 (d, 1H, J=2.4 Hz), 8.07 (s, 1H), 8.02-7.92 (m, 6H), 7.78 (d, 1H, J=2.4 Hz), 7.64 (d, 2H, J=8.4 Hz), 7.44 (bs, 1H), 6.11 (bs, 2H) and 3.24 (s, 3H). LC-MS APCI: Calculated for C19H17N3O3S, 367; Observed m/z 368 [M+H]+.

Workup

  1. customobtained
  2. additionpoured onto H2O (10 mL)
  3. extractionextracted with MeOH/CHCl3 (1:4) (3×20 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-3519f2c506324b2e9b51062b9419a76b
Source dataset
uspto-grants-2015_05
Patent number
US09024033B2

Reaction notes

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