Hydrazine hydrate (1:1) → HCID 178489372, compound

HRID 886614Notes

Reaction equation

HRID 886614 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=O)[C:5](F)=[N:6][CH:7]=1.O.[NH2:20][NH2:21]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:21][NH:20][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59825042(5-Bromo-2-fluoro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone

Product 1

HCID 178489372HCID 178489372, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (5-bromo-2-fluoro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone (1.9 g, 6.1 mmol) in ethanol (125 ml), hydrazine monohydrate (691 μl, 12.2 mmol) was added and the resulting solution was allowed to stir at room temperature overnight. Solvent was removed under reduced pressure and the product was precipitated out by addition of water to afford 5-bromo-3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridine (1.1 g, 58% yield). 1H NMR (500 MHz, DMSO-d6) δ 3.84 (s, 3H), 7.07 (m, 1H), 7.20 (d, 1H), 7.45 (m, 1H), 7.62 9d, 1H), 8.34 (s, 1H), 8.60 (s, 1H). MS: m/z 304+306 (M+H+).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe product was precipitated out by addition of water

Sources & evidence

ORD record
ord-40d66947a7b4475995b3bf1fb3ee00a0
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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