Pyridine → 2,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide

HRID 40538Notes

Reaction equation

HRID 40538 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>ClCCl>[CH3:24][C:23]([CH3:26])([CH3:25])[C:22]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][N:13]=1)=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 468541905-Phenylethynyl-pyridin-2-ylamine

Product 1

HCID 715482442,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamideYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(65 mg, 0.33 mmol) 5-Phenylethynyl-pyridin-2-ylamine (Example 1, step 1) was dissolved in dichloromethane (3 ml). Pyridine (52 mg, 53 μl, 0.67 mmol, 2 equiv.) and pivaloyl chloride (48 mg, 50 μl, 0.40 mmol, 1.2 equiv.) were added and the mixture was stirred for 2 hours at room temperature. The reaction mixture was extracted with 1N HCl solution and twice with dichloromethane. The organic extracts were combined, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with heptane:dichloromethane 50:50. The desired 2,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide (40 mg, 43% yield) was obtained as a light yellow solid, MS: m/e=279.3 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with 1N HCl solution and twice with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography on a silica gel column
  5. washeluting with heptane:dichloromethane 50:50

Sources & evidence

ORD record
ord-f7268b02a0e74b34b0bacc1c837740c9
Source dataset
uspto-grants-2013_09
Patent number
US08530472B2

Reaction notes

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