Dichloromethane → HCID 68290880, compound

HRID 2205947Notes

Reaction equation

HRID 2205947 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:4]=1[NH2:5].Br[C:20]1[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:20]2[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=2)[CH:7]=[CH:6][C:4]=1[NH2:5]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 1674331H-Pyrazole, 4-bromo-1-methyl-HCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 68290880HCID 68290880, compoundYield 70.4%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5 g, 24.03 mmol), 4-bromo-1-methyl-1H-pyrazole (3.53 g, 17.47 mmol), Pd(dppf)Cl2.DCM (0.38 g, 0.465 mmol) and 2M sodium carbonate (20 ml0 in THF (60 ml) was stirred and heated to 60° C. for 24 hours. The reaction was diluted with ethyl acetate and brine. The organic solution was collected, dried (MgSO4) and concentrated in vacuum. The residue was purified using Biotage silica gel column chromatography eluting with a gradient of 0 to 70% ethyl acetate in cyclohexane to afford the title compound as a white powder (2.5 g, 70%). 1H NMR (500 MHz, CDCl3) δ 3.8 (s, br, 2H), 3.9 (s, 3H), 3.94 (s, 3H), 6.71 (d, J=7.9 Hz, 1H), 6.9 (m, 2H), 7.52 (s, 1H), 7.68 (s, 1H).

Workup

  1. customThe organic solution was collected
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified
  5. washeluting with a gradient of 0 to 70% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-404c541a8eb7415792e0804285ef6344
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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