Boron tribromide → HCID 17747408, compound

HRID 889281Notes

Reaction equation

HRID 889281 reaction equation
C([O:8][C:9]1[C:10]([N:29]2[S:33](=[O:35])(=[O:34])[NH:32][C:31](=[O:36])[CH2:30]2)=[C:11]([F:28])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19]CC1C=CC=CC=1)=[C:14]([Br:27])[CH:13]=2)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[Br:27][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:9]([OH:8])[C:10]([N:29]3[S:33](=[O:35])(=[O:34])[NH:32][C:31](=[O:36])[CH2:30]3)=[C:11]2[F:28])=[CH:16][C:15]=1[OH:19]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68430767HCID 68430767, compound

Product 1

HCID 17747408HCID 17747408, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(3,6-bis-benzyloxy-7-bromo-1-fluoronaphthalen-2-yl)-1,1-dioxo-[1,2,5]thiadiazolidin-3-one (232 mg, 0.406 mmol) in CH2Cl2 (3 mL) at 0° C. under nitrogen is added BBr3 (0.731 mL, 0.731 mmol). The reaction is stirred at 0° C. for 5 min then the mixture is quenched with 1N HCl (50 mL) and is extracted 3 times with EtOAc, dried over Na2SO4 and washed with brine. The organic layer is concentrated under reduced pressure and purified on reverse phase HPLC using a gradient of 10-20% MeCN/water (0.1% TFA).

Workup

  1. customthe mixture is quenched with 1N HCl (50 mL)
  2. extractionis extracted 3 times with EtOAc
  3. dry with materialdried over Na2SO4
  4. washwashed with brine
  5. concentrationThe organic layer is concentrated under reduced pressure
  6. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-39f44cdec07b44f696a9be502efa5dab
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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