Boron tribromide → HCID 25271234, compound

HRID 1516413Notes

Reaction equation

HRID 1516413 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH2:40][CH2:41][O:42]C)(=[N:29]C(OCC3C=CC=CC=3)=O)=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH2:40][CH2:41][OH:42])(=[NH:29])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86652064HCID 86652064, compound

Product 1

HCID 25271234HCID 25271234, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-(2-methoxyethyl)-N-benzyloxycarbonyl sulfoximide (0.3 g, 0.00046 mol) in DCM (3 mL) was added 1M solution of BBr3 in DCM(0.33 g, 0.00138 mol) at −70° C. under nitrogen atmosphere. Reaction mixture was stirred for 3 hr at 25-30° C. Subsequent work up and column purification (2% methanol in chloroform and 100-200 mesh silica gel) gave 65 mg of desired product in 28% yield.

Workup

  1. customReaction mixture
  2. customSubsequent work up and column purification (2% methanol in chloroform and 100-200 mesh silica gel)

Sources & evidence

ORD record
ord-520fce2415ff41e79b28d749cd4c6dda
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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