Tetrahydrofuran → 2-[5-[(4-Cyano-2-methylphenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylic acid

HRID 878658Notes

Reaction equation

HRID 878658 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[N:15]([C:16]3[CH:21]=[C:20]([C:22]([O:24]C)=[O:23])[CH:19]=[CH:18][N:17]=3)[N:14]=[CH:13][CH:12]=2)=[C:5]([CH3:26])[CH:4]=1)#[N:2].O[Li].O.C1COCC1>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[N:15]([C:16]3[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][N:17]=3)[N:14]=[CH:13][CH:12]=2)=[C:5]([CH3:26])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86725618Methyl 2-[5-[(4-cyano-2-methylphenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate

Product 1

HCID 867256192-[5-[(4-Cyano-2-methylphenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Charged methyl 2-[5-[(4-cyano-2-methylphenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate (112 mg, 0.32 mmol), LiOH.H2O (14 mg, 0.32 mmol), water (2 mL) and THF (2 mL) to a flask, then the mixture was stirred at room temperature for 30 min, added another 2 mL water, and the mixture was washed with ethyl acetate twice (6 mL×2). The aqueous phase was acidified with 1N HCl (pH=3), filtered and dried the solid to give the title compound. 1H NMR (300 MHz, DMSO-d6): δ 2.37 (3H, s), 5.37 (2H, s), 6.10 (1H, d, J=1.8 Hz), 7.62 (1H, d, J=1.5 Hz), 7.70-7.77 (4H, m), 8.08 (1H, s), 8.68 (1H, d, J=5.4 Hz). [M+H] Calc'd for C18H14N4O3, 335; Found, 335.

Workup

  1. washthe mixture was washed with ethyl acetate twice (6 mL×2)
  2. filtrationfiltered
  3. customdried the solid

Sources & evidence

ORD record
ord-f92766b86b4e4beeba513ce4d2fa0a72
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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