2-(4-cyclopropyl-1H-pyrazol-1-yl)-5-nitropyridine → 6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-amine

HRID 537580Notes

Reaction equation

HRID 537580 reaction equation
[CH:1]1([C:4]2[CH:5]=[N:6][N:7]([C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=3)[CH:8]=2)[CH2:3][CH2:2]1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH:1]1([C:4]2[CH:5]=[N:6][N:7]([C:9]3[N:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 681576882-(4-cyclopropyl-1H-pyrazol-1-yl)-5-nitropyridine

Product 1

HCID 681567276-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-amineYield 38%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-cyclopropyl-1H-pyrazol-1-yl)-5-nitropyridine (2.91 g, 12.7 mmol) in ethyl acetate (250 ml) was passed through an H-Cube reactor equipped with a 10% Pd(OH)2/C cartridge at 50° C., 50 bar, at 1 ml/min. The solution was concentrated in vacuo. The crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane) to yield the product (964 mg, 38%) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.85 (d, J=2.7 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.48 (s, 1H), 7.12 (dd, J=8.7, 2.8 Hz, 1H), 3.70 (br. s., 2H), 1.75 (tt, J=8.6, 5.3 Hz, 1H), 0.88 (ddd, J=8.4, 6.3, 4.5 Hz, 1H), 0.59 (dt, J=5.7, 4.5 Hz, 2H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThe crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-932622906a934daa9a90f3c0f296abfb
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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