Sodium Carbonate → HCID 22135533, compound

HRID 2113084Notes

Reaction equation

HRID 2113084 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O>[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:2]2[N:7]=[N:6][C:5]([NH:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[N:16]4)=[CH:11][CH:10]=3)=[CH:4][C:3]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 201262(4-Methoxyphenyl)boronic acid2×HCID 22135529HCID 22135529, compound

Product 1

HCID 22135533HCID 22135533, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [6-chloro-5-(4-trifluoromethylphenyl)pyridazin-3-yl]-[quinolin-7-yl]amine, Example 88, (100 mg, 0.3 mmol) in dioxane (2 mL) was added 4-methoxyphenylboronic acid (46 mg, 0.3 mmol, Aldrich), followed by the addition of 2M aq Na2CO3 (0.2 mL, 0.4 mmol) and Pd[PPh3]4 (35 mg, 0.03 mmol, Aldrich). The mixture was flushed with N2 and heated under at 100° C. under N2 atmosphere for 24 h. The reaction mixture was cooled to room temperature, additional amounts of 2M aq Na2CO3 (0.2 mL, 0.4 mmol), 4-methoxyphenyl-boronic acid (46 mg, 0.3 mmol) and Pd[PPh3]4 (35 mg, 0.03 mmol) were added and the mixture was heated at 100° C. with stirring under N2 atmosphere for 4 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL) and washed with 5% Na2CO3. The organic layer was dried over Na2SO4, filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography, eluting with MeOH:CH2Cl2 (1:19), to give the title compound as a tan crystalline solid. MS (ESI, pos. ion) m/z: 473 (M+1). MP: 215-217° C.

Workup

  1. customThe mixture was flushed with N2
  2. temperatureThe reaction mixture was cooled to room temperature
  3. temperaturethe mixture was heated at 100° C.
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed with 5% Na2CO3
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluting with MeOH:CH2Cl2 (1:19)

Sources & evidence

ORD record
ord-dab52c48696e4cc08c73e66efe428087
Source dataset
uspto-grants-2009_04
Patent number
US07524874B2

Reaction notes

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