Potassium Carbonate → HCID 44525560, compound

HRID 571012Notes

Reaction equation

HRID 571012 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:9]=[C:10]([C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[C:11]([NH2:14])=[N:12][CH:13]=1.[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])=[O:25]>O1CCOCC1>[CH3:22][O:21][C:18]1[N:17]=[CH:16][C:15]([C:10]2[C:11]([NH2:14])=[N:12][CH:13]=[C:8]([C:30]3[CH:31]=[CH:32][C:27]([S:24]([CH3:23])(=[O:26])=[O:25])=[CH:28][CH:29]=3)[CH:9]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 67324047HCID 67324047, compound

Product 1

HCID 44525560HCID 44525560, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

K2CO3 aqueous solution (1 M, 5.4 mL) was added to a suspension of 5-bromo-3-(6-methoxypyridin-3-yl)pyridin-2-amine (1.44 g, 5.14 mmol), 4-(methylsulfonyl)phenyl boronic acid (1.08 g, 5.40 mmol, 1.05 equiv.), and Pd(PPh)3 (300 mg, 5 mol %) in dioxane (15 mL) under N2. The reaction mixture was stirred at 120° C. for 14 h, poured onto H2O (50 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/EtOAc, 2/8) providing 3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine (1) (1.92 g, 65%) as a pale yellow solid. IR (thin film/cm−1): νmax 3378, 1594, 1301, 1148. H1 NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, J=2.0 Hz), 8.26 (d, 1H, J=2.0 Hz), 7.97 (d, 2H, J=8.4 Hz), 7.70 (d, 2H, J=8.4 Hz), 7.69 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=2.0 ), 6.86 (d, 1H, J=8.4 Hz), 4.80 (bs, 2H), 3.98 (s, 3H) and 3.06 (s, 3H). C13 NMR (100 MHz, CDCl3): δ 164.16, 156.30, 146.94, 146.82, 145.57, 143.34, 139.02, 138.86, 136.92, 128.17, 126.84, 125.84, 118.88, 111.49, 53.67 and 44.62.

Workup

  1. additionpoured onto H2O (50 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (hexane/EtOAc, 2/8)

Sources & evidence

ORD record
ord-251b40fedf92417a9cb5871231f81226
Source dataset
uspto-grants-2015_05
Patent number
US09024033B2

Reaction notes

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