Phosphorus tribromide → 6-(Bromomethyl)-2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 2272831Notes

Reaction equation

HRID 2272831 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:19]=[C:12]2[CH:13]=[CH:14][C:15]([CH2:17]O)=[CH:16][N:11]2[N:10]=1.P(Br)(Br)[Br:21]>C(Cl)Cl>[Br:21][CH2:17][C:15]1[CH:14]=[CH:13][C:12]2[N:11]([N:10]=[C:9]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=3[CH3:8])[N:19]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 118129975(2-(2,6-Dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol

Product 1

HCID 1181299826-(Bromomethyl)-2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol (148 g, 0.584 mol) in DCM (2.96 L) is added PBr3 (237.3 g, 0.877 mol) at −40° C. The reaction mixture is allowed to warm to temperature and then stirred for a further for 2 hours at room temperature. The reaction is cooled to 0° C., quenched with ice cold water (1.5 L) and saturated sodium bicarbonate solution is added to adjust the pH ˜7.5 to 8. The mixture is diluted with DCM (2 L), the aqueous layer is separated and extracted with DCM (3 L). The organic extracts are combined, washed with water (2×3 L) and brine solution (3 L), dried the organic extracts over sodium sulphate, filtered and evaporated to dryness to give the title compound (140 g, 76%). LCMS m/z 316/318 79Br/81Br (M+H)+.

Workup

  1. temperatureto warm to temperature
  2. temperatureThe reaction is cooled to 0° C.
  3. customquenched with ice cold water (1.5 L) and saturated sodium bicarbonate solution
  4. additionis added
  5. additionThe mixture is diluted with DCM (2 L)
  6. customthe aqueous layer is separated
  7. extractionextracted with DCM (3 L)
  8. washwashed with water (2×3 L) and brine solution (3 L)
  9. dry with materialdried the organic extracts over sodium sulphate
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-0b087ed8372a4d7e82075683bc60dd21
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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