Boron tribromide → HCID 178472419, compound

HRID 2202745Notes

Reaction equation

HRID 2202745 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:5][N:6]([CH2:29][C:30]([C:32]1[C:37]([O:38]C)=[CH:36][CH:35]=[CH:34][C:33]=1[O:40][CH3:41])=[O:31])[C:7]([C:9]1[CH:10]=[N:11][N:12]([C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13]=1[C:14]([F:17])([F:16])[F:15])=[O:8].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:5][N:6]([CH2:29][C:30]([C:32]1[C:33]([O:40][CH3:41])=[CH:34][CH:35]=[CH:36][C:37]=1[OH:38])=[O:31])[C:7]([C:9]1[CH:10]=[N:11][N:12]([C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13]=1[C:14]([F:15])([F:17])[F:16])=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178472420HCID 178472420, compound

Product 1

HCID 178472419HCID 178472419, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 7-3 (50 mg, 0.07 mmol) in DCM (5 mL) was added BBr3 (1.0 M in DCM, 1.5 mL, 1.4 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 7-4 (32 mg, 65%) as a brown color gum.

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-cd7794e339a342f8bb783a4cc15c608c
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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