Methylhydrazine → HCID 86700217, compound

HRID 879412Notes

Reaction equation

HRID 879412 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=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:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 79018099HCID 79018099, compound

Product 1

HCID 86700217HCID 86700217, compound

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-3-yl)methanone (3.417 g, 12.2 mmol) and dioxane (30 mL). Methylhydrazine (1.4 mL, 26.6 mmol) was then added, and the mixture was heated to 100° C. for 16 hours. The crude mixture was concentrated, and purified by column chromatography (gradient 0 to 55% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 9.19 (d, J=2.1 Hz, 1H), 8.65 (dd, J=4.9, 1.5 Hz, 1H), 8.28 (d, J=8.0 Hz, 1H), 8.13 (d, J=1.6 Hz, 1H), 7.54 (dd, J=8.9, 1.7 Hz, 1H), 7.49 (dd, J=8.0, 4.9 Hz, 1H), 7.35 (d, J=8.9 Hz, 1H), 4.15 (s, 3H).

Workup

  1. concentrationThe crude mixture was concentrated
  2. custompurified by column chromatography (gradient 0 to 55% EtOAc in hexanes)
  3. customto give the product

Sources & evidence

ORD record
ord-7e3def0d05f54fc888c37456e35ae7bd
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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