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Ethyl Acetate → HCID 67123010, compound

HRID 2046385
Notes
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Reaction equation

HRID 2046385 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11](I)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCOCC1.O.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>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 469421452-Benzyl-5-iodopyridazin-3(2H)-one

Product 1

HCID 67123010HCID 67123010, compound

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent2×
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Benzyl-5-iodopyridazine-3(2H)-one (5.0 g, 16 mmol), 4-fluorophenyl boronic acid (2.91 g, 20.8 mmol), Pd(Ph3P)4 (0.93 g, 0.80 mmol), and potassium carbonate (6.64 g, 48.1 mmol) were combined in dioxane (120 ml) and Water (40 ml). The reaction mixture was refluxed at 100° C. for 3 h, cooled to room temperature, and poured into ethyl acetate (200 mL) and water (200 mL). The mixture was extracted with ethyl acetate (3×200 mL). The combined organics were washed with water, dried (sodium sulfate), concentrated, and purified by flash chromatography to afford the title compound as a white solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.38 (d, 1H); 7.25-7.92 (m, 10H); 5.27 (s, 2H). LRMS (APCI) calc'd for (C17H14FN2O) [M+H]+, 281.1. found 281.1.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organics were washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e696953cc84b46e899a7fc76b45869cc
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes