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Potassium Phosphate, Tribasic → HCID 10065775, compound

HRID 891937
Notes
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Reaction equation

HRID 891937 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]=1B(O)O.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[C:31]2[CH3:35])[N:26]=[N:27][CH:28]=1.Cl.CCOCC>C1(C)C=CC=CC=1.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.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[ClH:22].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]=1[C:23]1[CH:24]=[C:25]([CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[C:31]2[CH3:35])[N:26]=[N:27][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 10953452Ether hydrochlorideHCID 117890255-Chloro-3-(2-methylimidazol-1-ylmethyl)-pyridazineHCID 221764573,4-Dihydronaphthalen-2-ylboronic acid2×

Product 1

HCID 10065775HCID 10065775, compoundYield 60.3%

Reagents, catalysts & solvents 4

HCID 27342162-(Dicyclohexylphosphino)biphenylCatalyst2×
HCID 178418397HCID 178418397, compoundCatalyst2×
HCID 887MethanolSolvent
HCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.02 g, 0.017 mmol), biphenyl-2-yl-dicyclohexyl-phosphane (0.005 g, 0.014 mmol), K3PO4 (0.21 g, 1 mmol) and 3,4-dihydro-naphthalene-2-boronic acid (0.13 g, 0.7 mmol) were mixed in degassed toluene (2 ml). 5-Chloro-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine (0.1 g, 0.48 mmol) was added and the mixture was refluxed for 24 hours. After further addition of tetrakis(triphenylphosphine)palladium (0.02 g, 0.017 mmol), biphenyl-2-yl-dicyclohexyl-phosphane (0.005 g, 0.014 mmol) and 3,4-dihydro-naphthalene-2-boronic acid (0.13 g, 0.7 mmol) reflux was continued for another 12 hours. After removal of the solvent in vacuo the residue was dissolved in AcOEt, washed with H2O, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed over silica gel [gradient CH2Cl2 to 40% (CH2Cl2—MeOH—NH4OH 90:10:1)] to provide a white foam which was dissolved in MeOH (2 ml). HCl-Et2O was added to provide the title compound (0.098 g, 40%) as a light yellow solid, MS: m/e=303.3 (M+).

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperaturereflux
  3. customAfter removal of the solvent in vacuo the residue
  4. dissolutionwas dissolved in AcOEt
  5. washwashed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed over silica gel [gradient CH2Cl2 to 40% (CH2Cl2—MeOH—NH4OH 90:10:1)]
  9. customto provide a white foam which

Sources & evidence

ORD record
ord-648c5b2f3e2a4169beab2907a5f2a38b
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07005432B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes