Potassium Carbonate → HCID 22240218, compound

HRID 891874Notes

Reaction equation

HRID 891874 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])[N:5]=[N:6][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[F:22].C([O-])([O-])=O.[K+].[K+].Cl.CCOCC>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:1].[Cl:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:3]=[C:4]([CH2:8][N:9]3[CH:13]=[CH:12][N:11]=[C:10]3[CH3:14])[N:5]=[N:6][CH:7]=2)[CH:19]=[CH:20][C:21]=1[F:22]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 10953452Ether hydrochlorideHCID 117890255-Chloro-3-(2-methylimidazol-1-ylmethyl)-pyridazine

Product 1

HCID 22240218HCID 22240218, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

5-Chloro-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine (0.07 g, 0.34 mmol), 3-chloro-4-fluorophenylboronic acid (0.076 g, 0.44 mmol), K2CO3 (0.09 g, 0.67 mmol) and tetrakis(triphenylphosphine)palladium (0.04 g, 0.034 mmol) were mixed and degassed dioxane (1.4 ml) was added. The mixture was refluxed for 44 hours and the solvent was removed in vacuo. The residue was taken in MeCl2, filtrated and the filtrate was concentrated in vacuo. The residue was chromatographed over silica gel (CH2Cl2—MeOH 98:02) to provide a white foam which was dissolved in MeOH (2 ml). HCl-Et2O was added to provide 5-(3-chloro-4-fluoro-phenyl)-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine hydrochloride (0.1 g, 77%) as an offwhite solid, MS: m/e=302.7 (M+).

Workup

  1. customdegassed dioxane (1.4 ml)
  2. additionwas added
  3. temperatureThe mixture was refluxed for 44 hours
  4. customthe solvent was removed in vacuo
  5. filtrationfiltrated
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed over silica gel (CH2Cl2—MeOH 98:02)
  8. customto provide a white foam which

Sources & evidence

ORD record
ord-6106e19b7deb486bafe95517f7510166
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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