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Cesium carbonate → 2-(2,2,2-Trifluoroethyl)-4-(2-propoxy)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone

HRID 1241748
Notes
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Reaction equation

HRID 1241748 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][N:4]1[C:9](=[O:10])[C:8]([O:11][CH:12]([CH3:14])[CH3:13])=[C:7](Br)[CH:6]=[N:5]1.[CH3:18][S:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.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>[F:1][C:2]([F:17])([F:16])[CH2:3][N:4]1[C:9](=[O:10])[C:8]([O:11][CH:12]([CH3:14])[CH3:13])=[C:7]([C:23]2[CH:24]=[CH:25][C:20]([S:19][CH3:18])=[CH:21][CH:22]=2)[CH:6]=[N:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 219339302-(2,2,2-trifluoroethyl)-4-(2-propoxy)-5-bromo-3(2H)-pyridazinone

Product 1

HCID 539239392-(2,2,2-Trifluoroethyl)-4-(2-propoxy)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinoneYield 81%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-(2,2,2-trifluoroethyl)-4-(2-propoxy)-5-bromo-3(2H)-pyridazinone (1.2 g, 3.8 mmol), 4-(methylthio)phenylboronic acid (704 mg, 4.19 mmol), tetrakis(triphenylphosphine)palladium(0) (220 mg, 5% mmol) and cesium carbonate (2.72 g, 8.3 mmol) in 20 mL of ethylene glycol dimethyl ether was heated to reflux for 5 hours. The mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water, brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (94:6 hexanes/ethyl acetate). The product was obtained as a greenish solid (yield: 1.1 g, 81%). 1H NMR (300 MHz, CDCl3) δ 1.19 (d, J=7.5 Hz, 6H), 2.55 (s, 3H), 4.83 (q, J=9 Hz, 2H), 5.28 (h, J=6 Hz, 1H), 7.32 (d, J=9 Hz, 2H), 7.52 (d, J=9 Hz, 2H), 7.85 (s, 1H). MS (DCI) m/z 359 (M+H)+.

Workup

  1. temperatureto reflux for 5 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (94:6 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-3fc7a5fe1d06427a98fb00546da9d433
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07115591B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes