Benzyl Alcohol → 2-[5-(benzyloxy)-1H-pyrazol-1-yl]pyridine-4-carbonitrile

HRID 514382Notes

Reaction equation

HRID 514382 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][CH:3]=1.[C:15]1([CH2:21]O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[CH2:21]([O:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][CH:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178510213HCID 178510213, compound

Product 1

HCID 867255112-[5-(benzyloxy)-1H-pyrazol-1-yl]pyridine-4-carbonitrileYield 21.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carbonitrile (186 mg, 1 mmol), phenylmethan-1-ol (216 mg, 2 mmol), and PPh3 (523 mg, 2 mmol) in THF (10 mL) was added dropwise DIAD (402 mg, 2 mmoL) at 0° C. under N2. Then the mixture was stirred at rt overnight. Water was added, and the reaction mixture was extracted with EtOAc, then washed with water and brine. The organic phase was dried, concentrated, and purified by prep-HPLC to afford the title compound (60 mg). 1H NMR (400 MHz, CDCl3): δ 5.25 (2H, s), 5.75 (1H, d, J=2.0 Hz), 7.36-7.44 (5H, m), 7.57 (1H, d, J=2.0 Hz), 8.04 (1H, s), 8.71 (1H, d, J=5.2 Hz). [M+H] Calc'd for C16H12N4O, 277. Found, 277.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washwashed with water and brine
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-8112b22090da45c3a7a072575a9c8da0
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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