Methanol → HCID 135949498, compound

HRID 1639699Notes

Reaction equation

HRID 1639699 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]([NH2:17])=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)[N:14]=[N:13]1.B(Br)(Br)Br.CO.[OH-].[Na+]>ClCCl.O>[NH2:17][C:16]1[N:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[Cl:1])[N:13]=[N:14][C:15]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 25154238HCID 25154238, compound

Product 1

HCID 135949498HCID 135949498, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-(2-chloro-4-trifluoromethyl-phenyl)-5-(4-methoxy-phenyl)-3H-[1,2,3]triazol-4-ylamine (3) (1.000 g, 2.7119 mmol) in anhydrous dichloromethane (20 ml), cooled to −78° C. and under a nitrogen flow, a solution of boron tribromide (11.5497 g, ˜4.36 ml, 46.1023 mmol) in 10 ml of anhydrous dichloromethane is added drop-wise. The mixture is allowed to reach room temperature spontaneously overnight and it is then cooled again in an ice-salt bath and the excess of the reagent is decomposed upon drop-wise addition of 10 ml of methanol and 10 ml of water. After 10 min stirring, 10% sodium hydroxide solution (20 ml) is added and the aqueous layer, once separated, is acidified with 10% hydrochloric acid solution and extracted with chloroform (3×70 ml). The combined organic layers are dried over MgSO4, filtered and evaporated to afford a solid grey residue (0.800 g, 83% yield, 99.47% pure at HPLC). M.p. 161-162.3° C. LC-ESI-HRMS of [M+H]+ shows 355.0579 Da. Calc. 355.057348 Da, dev. 1.6 ppm.

Workup

  1. temperatureit is then cooled again in an ice-salt bath
  2. customthe aqueous layer, once separated
  3. extractionextracted with chloroform (3×70 ml)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid grey residue (0.800 g, 83% yield, 99.47% pure at HPLC)

Sources & evidence

ORD record
ord-7868a7dafe314b6ea75cd22f3d5d84c6
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

Loading…