Boron tribromide → HCID 118159589, compound

HRID 628263Notes

Reaction equation

HRID 628263 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:16]([CH3:19])=[N:17][N:18]=3)[C:10]=2[CH:9]=[C:8]1[CH3:20].B(Br)(Br)Br>C(Cl)Cl>[CH3:19][C:16]1[N:15]2[C:10]3[CH:9]=[C:8]([CH3:20])[N:7]([CH2:6][C:5]4[CH:4]=[C:3]([OH:2])[CH:23]=[CH:22][CH:21]=4)[C:11]=3[CH:12]=[CH:13][C:14]2=[N:18][N:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118159718HCID 118159718, compound

Product 1

HCID 118159589HCID 118159589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 6-(3-methoxybenzyl)-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (0.030 g, 0.098 mmol, from Example 22) in DCM (4 mL) at −78° C. was added 1.0 M BBr3 in DCM (0.57 mL, 0.57 mmol, Aldrich) and the mixture was allowed to warm to ambient temperature. The reaction was quenched by the addition of water, and saturated NaHCO3 solution was added. DCM was removed by rotary evaporation and the aqueous mixture was diluted with MeOH, filtered and purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.02 g, 70%).

Workup

  1. customThe reaction was quenched by the addition of water, and saturated NaHCO3 solution
  2. additionwas added
  3. customDCM was removed by rotary evaporation
  4. additionthe aqueous mixture was diluted with MeOH
  5. filtrationfiltered
  6. custompurified by preparative HPLC-MS (Waters XBridge C18
  7. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.02 g, 70%)

Sources & evidence

ORD record
ord-812f4633e3a34f6d9b0b6bd8be9f4f1f
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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