Sodium Carbonate → HCID 67004105, compound

HRID 1663186Notes

Reaction equation

HRID 1663186 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(CC)CC)[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[N+:9]([C:5]1[C:4]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:3][C:2]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 67004761HCID 67004761, compound

Product 1

HCID 67004105HCID 67004105, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-2-nitro-3-pyrazol-1-yl-phenylamine (200 mg, 0.71 mmol) in THF (8 mL) was added, successively, 3-pyridyl-diethyl borane (157 mg), (tetrakistriphenylphosphine) palladium(0) (84 mg), and sodium carbonate (1.1 mL, 2.2 mmom of 2M aqueous). The resulting mixture was stirred at 70° C. overnight then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (50 mL), brine (50 mL), dried (MgSO4) then concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with a gradient of ethyl acetate:hexanes (1:3, 1:2, 1:0, 2:1, 4:1, 8:1), to afford 120 mg (60%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 6.45 (br, s 2H), 6.55 (t, 1H), 7.1 (s, 1H), 7.25 (s, 1H), 7.55 (m, 1H), 7.7 (s, 1H), 8.1 (dt, 1H), 8.3 (d, 1H), 8.7 (d, 1H), 8.9 (s, 1H).

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationthen concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography over silica gel
  6. washeluted with a gradient of ethyl acetate:hexanes (1:3, 1:2, 1:0, 2:1, 4:1, 8:1)

Sources & evidence

ORD record
ord-db81d029d5c44d65bbed55b67f0d7a8e
Source dataset
uspto-grants-2011_10
Patent number
US08034832B2

Reaction notes

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