Triphenylphosphine → 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide

HRID 1454827Notes

Reaction equation

HRID 1454827 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]([F:45])([F:44])[C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH3:13][C:11]([CH3:12])([CH3:14])[C:10]([NH:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][O:1][C:40]2[CH:41]=[CH:42][C:37]([C:36]([F:45])([F:44])[F:35])=[CH:38][CH:39]=2)[N:8]=1)=[O:15]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21782926N-[6-(Hydroxymethyl)pyridin-2-yl]-2,2-dimethylpropanamide

Product 1

HCID 688432242,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamideYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(6-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (0.625 g), triphenylphophine (0.786 g) and 4-trifluoromethyl-phenol (0.486 g) in toluene was treated at RT under an argon atmosphere with diisopropyl azodicarboxylate (0.67 g). The mixture was stirred for 2 h, partitioned between ice water and AcOEt, the layers were separated, the aqueous layer twice extracted with AcOEt. The combined organic layers were washed with water and saturated aqueous NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100 to 85%) to give 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide (0.98 g) as a yellow oil. MS (ESI): 353.2 (MH+).

Workup

  1. custompartitioned between ice water and AcOEt
  2. customthe layers were separated
  3. extractionthe aqueous layer twice extracted with AcOEt
  4. washThe combined organic layers were washed with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography (heptane/AcOEt 100 to 85%)

Sources & evidence

ORD record
ord-95b6212040154c8ea5f1448012f0e1a4
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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