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3-Pyridinemethanol → HCID 66939421, compound

HRID 1257391
Notes
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Reaction equation

HRID 1257391 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([CH2:17][N:18]3[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[N:19]3)[S:15][CH:16]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34]O)[CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.O>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][O:1][C:2]2[CH:3]=[C:4]([C:12]3[N:13]=[C:14]([CH2:17][N:18]4[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[N:19]4)[S:15][CH:16]=3)[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=2)[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66939232HCID 66939232, compound

Product 1

HCID 66939421HCID 66939421, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (7 mL) of the compound (300 mg, 0.75 mmol) obtained in Example 86a, 3-pyridinemethanol (0.088 mL, 0.91 mmol) and triphenylphosphine (260 mg, 0.98 mmol) in tetrahydrofuran was added diisopropyl azodicarboxylate (1.9M toluene solution, 0.51 mL, 0.98 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50) to give the title compound (370 mg, 100%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-657b83ba493c499391f306a73712bbea
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461348B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes