Triethylamine → HCID 58542035, compound

HRID 1966792Notes

Reaction equation

HRID 1966792 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:7]([C:9]3[CH:10]=[C:11]([CH2:20][OH:21])[CH:12]=[CH:13][C:14]=3[N:15]3[CH:19]=[N:18][CH:17]=[N:16]3)=[N:8][C:4]=2[CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:22]([CH3:24])([CH3:23])[CH3:25])[C:7]([C:9]3[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=3[N:15]3[CH:19]=[N:18][CH:17]=[N:16]3)[CH2:20][O:21][S:29]([CH3:28])(=[O:31])=[O:30])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58542017HCID 58542017, compound

Product 1

HCID 58542035HCID 58542035, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask is added [3-(5-bromo-1-tert-butyl-1H-benzoimidazol-2-yl)-4-[1,2,4]triazol-1-yl-phenyl]methanol (583 mg, 1.4 mmol) in CH2Cl2 (5 mL), followed by the addition of methansulfonyl chloride (0.15 mL, 1.9 mmol) and triethylamine (0.4 mL, 2.9 mmol). The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with saturated NaHCO3 (10 mL), extracted with EtOAc (3×10 mL). The organic layer is separated, washed with brine, dried under anhydrous Na2SO4 (500 mg), filtered and concentrated to afford methanesulfonic acid 3-(5-bromo-1-tert-butyl-1H-benzoimidazol-2-yl)-4-[1,2,4]-triazol-1-yl-benzyl ester (690 mg, 100%).

Workup

  1. customThe reaction mixture is quenched with saturated NaHCO3 (10 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. customThe organic layer is separated
  4. washwashed with brine
  5. customdried under anhydrous Na2SO4 (500 mg)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10ceca90a2394f6293a1ccedaeb5ac7a
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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