Sodium Carbonate → 2-[6-(4-ethyl-phenyl)-pyridin-3-yl]-N-(3-fluoro-benzyl)-acetamide

HRID 882950Notes

Reaction equation

HRID 882950 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[O:10])=[CH:4][CH:3]=1.[CH2:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)[CH3:21].C([O-])([O-])=O.[Na+].[Na+]>COCOC.O>[CH2:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[O:10])=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)[CH3:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 862487322-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-benzyl)-acetamide

Product 1

HCID 115954532-[6-(4-ethyl-phenyl)-pyridin-3-yl]-N-(3-fluoro-benzyl)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8020DimethoxymethaneSolvent2×

Procedure

2-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-benzyl)-acetamide and (0.125 gm, 0.5 mmole), 4-ethylbenzeneboronic acid (0.083 gm, 0.55 mmole) was dissolved in dimethoxymethane (DME), Na2CO3 (0.11 gm, 1 mmole) in 5 ml of water was added to the DME solution, the solution was then degassed for 30 min (Ar through the solution and vacuum applied for the first 5 min), Palladiumtetrakistriphenylphosphine (0.029 gm, 0.025 mmole) was added, degassed for additional 15 min, refluxed for 24 hr. The reaction was allowed to cool to room temperature, filtered, solid washed with ethyl acetate; the organic layer was dried, evaporated. The residue was chromatographed using ethyl acetate/hexane 3:2. The product is white solid (0.08 gm, 47%). H1-NMR INOVA-500 (DMSO d6) δ 1.228 (t, J=7.5 Hz, 3H), 2.669 (q, J=7.5 Hz, 2H), 3.590 (s, 2H), 4.321 (d, J=6 Hz, 2H), 7.053-7.113 (m, 3H), 7.324-7.375 (m, 3H), 7.766 (dd, J=9.0, 2.0 Hz, 1H), 7.887 (d, J=8.5 Hz, 1H), 7.994 (d, J=8.0 Hz, 2H), 8.548 (s, 1H), 8.696 (t, J=5.5 Hz, 1H). MS (m/z) 349.3 (M+H)+.

Workup

  1. customthe solution was then degassed for 30 min (Ar through the solution and vacuum
  2. customapplied for the first 5 min
  3. additionwas added
  4. customdegassed for additional 15 min
  5. temperaturerefluxed for 24 hr
  6. filtrationfiltered
  7. washsolid washed with ethyl acetate
  8. customthe organic layer was dried
  9. customevaporated
  10. customThe residue was chromatographed

Sources & evidence

ORD record
ord-8cfb76e7feeb4fa28523e8f79c5b0839
Source dataset
uspto-grants-2012_08
Patent number
US08236799B2

Reaction notes

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