Methylamine → HCID 178482620, compound

HRID 1487498Notes

Reaction equation

HRID 1487498 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[C:9]([F:12])([F:11])[F:10])=[N:6][CH:7]=1.[CH3:14][NH2:15]>C(=O)(O)[O-].[Na+].[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](=[N:15]\[CH3:14])/[C:9]([F:12])([F:11])[F:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 672952111-(5-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 178482620HCID 178482620, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 1-(5-Bromo-pyridin-2-yl)-2,2,2-trifluoro-ethanone (1.0 g, 3.93 mol) and methylamine (20 ml, tetrahydrofuran solution) is added titanium ethoxide (0.987 g, 4.33 mmole) at 0° C. then stirred at room temperature for 2 hours. Reaction mixture is diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by column chromatography eluting in 20% ethyl acetate in hexane to give the title compound (0.10 g). 1H-NMR (400 MHz, DMSO) δ: 3.25-3.26 (m, 3H), 7.85-7.90 (m, 2H), 8.49 (s, 1H). LC-MS (m/z): [M+H]=266.8.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washeluting in 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-66acb0177b6c4fa3b69cab2ce5d3cb96
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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