Boron tribromide → HCID 69927927, compound

HRID 2039527Notes

Reaction equation

HRID 2039527 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([O:24]C)[CH:23]=1)[CH2:6][C:7]1[N:16]2[N:17]=[C:18]([NH2:20])[N:19]=[C:15]2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1.B(Br)(Br)Br>ClCCl>[NH2:20][C:18]1[N:19]=[C:15]2[N:16]([C:7]([CH2:6][C:5]3[CH:4]=[C:3]([OH:2])[CH:23]=[C:22]([OH:24])[CH:21]=3)=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[N:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67042932HCID 67042932, compound

Product 1

HCID 69927927HCID 69927927, compoundYield 759.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 5-(3,5-dimethoxy-benzyl)-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamine (0.10 g, 0.30 mmol), prepared as described in Example 4, in anhydrous dichloromethane (10 mL) was added dropwise, under argon, 1M BBr3 solution (3 mL, 3 mmol) in DCM at 0-5° C. The ice bath was removed and the mixture was stirred at room temperature overnight. The reaction was diluted with ethyl acetate and washed with NaHCO3 satured solution, then with water and brine. After drying over Na2SO4, the solvent was removed to give a crude that was crystallized twice from ethyl acetate to afford the title compound (0.70 g, 70% yield).

Workup

  1. customprepared
  2. additionwas added dropwise, under argon
  3. customat 0-5° C
  4. customThe ice bath was removed
  5. additionThe reaction was diluted with ethyl acetate
  6. washwashed with NaHCO3 satured solution
  7. dry with materialAfter drying over Na2SO4
  8. customthe solvent was removed
  9. customto give a crude that
  10. customwas crystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-0aa2aec9ac914807abbc105c08232a5d
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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