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Triethylamine → 2,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinoline

HRID 339019
Notes
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Reaction equation

HRID 339019 reaction equation
Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1.C[N:15]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[N:16]1.[F-].[Cs+].[CH2:31](N(CC)CC)C>C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[C:11]([CH3:12])[C:2]([N:16]3[CH:17]=[C:18]([CH3:31])[CH:19]=[N:15]3)=[CH:3][CH:4]=2)[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25953Cesium fluorideHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 455994557-Bromo-2,8-dimethylquinoline

Product 1

HCID 709842262,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinolineYield 99.5%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed tube a mixture of 7-bromo-2,8-dimethylquinoline (0.60 g, 2.54 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.06 g, 5.08 mmol), PdCl2(dppf)*dcm (0.208 g, 0.254 mmol), CsF (1.00 g, 6.61 mmol) and triethylamine (0.531 mL, 3.81 mmol) in isopropyl alcohol (17 mL) was heated at 100° C. on an oil bath for 6 hours. The mixture was cooled to ambient temperature and partitioned between water (25 mL) and ethyl acetate (50 mL). The solids were removed by filtration through a pad of Celite and washed with additional ethyl acetate. The layers were separated and the organic layer washed with brine and dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 25M; 25% ethyl acetate/hexane) to afford 2,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinoline (0.60 g, 91%).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between water (25 mL) and ethyl acetate (50 mL)
  3. customThe solids were removed by filtration through a pad of Celite
  4. washwashed with additional ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (Biotage 25M; 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7dbaf9571cd44f3aabf29fabc18452e5
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889704B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes