Boron tribromide → HCID 44193189, compound

HRID 2421256Notes

Reaction equation

HRID 2421256 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20]C)=[C:6]2[C:10]=1[N:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([F:19])[CH:12]=1)[CH:8]=[CH:7]2.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:19])[CH:12]=3)[CH:8]=[CH:7][C:6]=2[C:5]([OH:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 596279267-Chloro-1-(3-fluoro-4-methoxyphenyl)-4-methoxy-1H-indole

Product 1

HCID 44193189HCID 44193189, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole (D12) (533 mg, 1.75 mmol) in dichloromethane (50 mL) at −78° C. was added boron tribromide (1M solution in dichloromethane, 7 mL, 7.0 mmol). The reaction mixture was allowed to warm to room temperature and then quenched by the addition of methanol and then water and dichloromethane. After separation of the layers, the aqueous phase was re-extracted with dichloromethane. The combined organic layers were dried over magnesium sulphate, filtered and concentrated at reduced pressure. The product was partially purified by silica gel chromatography eluting with 5-70% ethyl acetate in hexane. The product was further purified by MDAP to yield the title compound (E7), (39 mg).

Workup

  1. customquenched by the addition of methanol
  2. customAfter separation of the layers
  3. extractionthe aqueous phase was re-extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe product was partially purified by silica gel chromatography
  8. washeluting with 5-70% ethyl acetate in hexane
  9. customThe product was further purified by MDAP

Sources & evidence

ORD record
ord-ed2327d00bc14e438d0af7e9ee215ab6
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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