Toluene → HCID 68864069, compound

HRID 660251Notes

Reaction equation

HRID 660251 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH2:13][OH:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH2:13][O:14][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([F:15])[CH:21]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

8

Reactant 5

HCID 1140TolueneHCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 68863615HCID 68863615, compound

Product 1

HCID 68864069HCID 68864069, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 5-chloro-2-(hydroxymethyl)nicotinate (step 4, 340 mg, 1.59 mmol), 3-fluorophenol (325 mg, 2.90 mmol), and triphenylphosphine (761 mg, 2.9 mmol) in tetrahydrofuran (10 ml) was added 40% solution of diethylazodicarboxylate in toluene (506 mg, 2.9 mmol) and the reaction mixture was stirred at room temperature for 5 hours. To the reaction mixture was added water and the whole mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (4/1) to afford 300 mg (56%) of the title compound:

Workup

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified
  5. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record
ord-b3145555beee4ceb9506560270e3e942
Source dataset
uspto-grants-2011_12
Patent number
US08084476B2

Reaction notes

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