Boron tribromide → HCID 178472418, compound

HRID 2202748Notes

Reaction equation

HRID 2202748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[C:3]=1[C:10](=[O:44])[CH2:11][N:12]([CH2:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[C:38]([F:43])[CH:37]=1)[C:13]([C:15]1[CH:16]=[N:17][N:18]([C@H:24]2[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]2)[C:19]=1[C:20]([F:23])([F:22])[F:21])=[O:14].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:10](=[O:44])[CH2:11][N:12]([CH2:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[C:38]([F:43])[CH:37]=1)[C:13]([C:15]1[CH:16]=[N:17][N:18]([C@H:24]2[CH2:25][CH2:26][C@H:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:29]2)[C:19]=1[C:20]([F:22])([F:23])[F:21])=[O:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178472408HCID 178472408, compound

Product 1

HCID 178472418HCID 178472418, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 15-3 (0.25 g, 0.39 mmol) in DCM (10 mL) was added BBr3 (1.0 M in DCM, 3.9 mL, 3.9 mmol) at room temperature and the mixture was stirred for 16 h. Solvent was evaporated under reduced pressure and the obtained residue was purified by column chromatography (silica gel, 30% EtOAc/hexane as eluent) to provide compound 15-4 (85 mg, 35%) as a yellow oil.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by column chromatography (silica gel, 30% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-b802120f748944c5aa7429c98a3d7058
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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