Bromine → HCID 17981779, compound

HRID 2252080Notes

Reaction equation

HRID 2252080 reaction equation
[Br:1]Br.[CH:3]([S:6]([N:9]1[C:13]2[CH:14]=[C:15]([C:18]3[N:22]([CH:23]4[CH2:25][CH2:24]4)[CH:21]=[N:20][C:19]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:33])(=[O:8])=[O:7])([CH3:5])[CH3:4]>C(Cl)(Cl)Cl>[CH:3]([S:6]([N:9]1[C:13]2[CH:14]=[C:15]([C:18]3[N:22]([CH:23]4[CH2:24][CH2:25]4)[C:21]([Br:1])=[N:20][C:19]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH2:33])(=[O:8])=[O:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 17981818HCID 17981818, compound

Product 1

HCID 17981779HCID 17981779, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Add bromine (0.34 mL, 6.545 mmol) dropwise over 5 minutes to a solution of 1-isopropylsulfonyl-2-amino-6-(1-(cyclopropyl)-4-(2-fluorophenyl)-imidazol-5-yl)-benzimidazole (2.61 g, 5.95 mmol) in chloroform (0.7 L) and stir for 18 hours. Wash with water, saturated sodium bicarbonate, dry with magnesium sulfate, filter and remove solvents under reduced pressure. Purify the residue on silica gel eluting with ethyl acetate/dichloromethane mixtures to provide the title compound (2.41 g). MS(ES+): m/z=518.0 (M+H)+

Workup

  1. washWash with water, saturated sodium bicarbonate
  2. dry with materialdry with magnesium sulfate
  3. filtrationfilter
  4. customremove solvents under reduced pressure
  5. customPurify the residue on silica gel eluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-5285ae85659040b29af2e378798af5be
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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