Dibromomethane → 2-Bromo-4-methyl-5-[[2-(1-methyl-1H-pyrazol-4-yl)-4-pyridinyl]oxy]pyridine

HRID 709962Notes

Reaction equation

HRID 709962 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[CH:6][N:5]=[C:4](N)[CH:3]=1.C(ON=O)(C)(C)C.[Br:29]CBr>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[Br:29][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 3024DibromomethaneHCID 10906Tert-Butyl nitriteHCID 686640964-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine

Product 1

HCID 904166262-Bromo-4-methyl-5-[[2-(1-methyl-1H-pyrazol-4-yl)-4-pyridinyl]oxy]pyridineYield 86%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example A2 (0.2 g, 0.71 mmol) in dibromomethane (5 mL) was treated with tetrabutylammonium bromide (0.92 g, 2.84 mmol) and t-butylnitrite (0.7 g, 7.11 mmol) and stirred at RT for 4 h. The mixture was diluted with EtOAc, washed successively with satd. NaHCO3, water, and brine, dried over Na2SO4 and concentrated to dryness to afford 2-bromo-4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine as off-white solid (0.21 g, 86%). MS (ESI) m/z: 345.1 (M+H+).

Workup

  1. washwashed successively with satd
  2. dry with materialNaHCO3, water, and brine, dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c5132f48ad7c4743a69060e34182d8a4
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

Loading…