Methylhydrazine → 5-bromo-1-methyl-3-(pyridin-2-yl)-1H-indazole

HRID 879422Notes

Reaction equation

HRID 879422 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=O)[CH:7]=1.[CH3:17][NH:18][NH2:19]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:18]([CH3:17])[N:19]=[C:8]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 79018065(5-Bromo-2-fluorophenyl)(pyridin-2-yl)methanone

Product 1

HCID 867002265-bromo-1-methyl-3-(pyridin-2-yl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A heavy wall pressure flask was charged with (5-bromo-2-fluorophenyl)(pyridin-2-yl)methanone (0.98 g, 3.5 mmol) and dioxane (10 mL). Methylhydrazine (0.4 mL, 7.7 mmol) was then added, and the mixture was heated to 100° C. for 15 hours. The crude mixture was concentrated, and purified by column chromatography (gradient 0 to 20% EtOAc in hexanes) to give the product. NMR (400 MHz, CDCl3) δ 8.84 (s, 1H), 8.73 (d, J=4.8 Hz, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.76 (t, J=7.7 Hz, 1H), 7.50 (d, J=8.8 Hz, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.24 (d, J=7.3 Hz, 1H), 4.12 (s, 3H).

Workup

  1. concentrationThe crude mixture was concentrated
  2. custompurified by column chromatography (gradient 0 to 20% EtOAc in hexanes)
  3. customto give the product

Sources & evidence

ORD record
ord-9fb837f00b274150aca50209af77087c
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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