Boron tribromide → HCID 86584086, compound

HRID 1168083Notes

Reaction equation

HRID 1168083 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:28])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([CH:25]([CH3:27])[CH3:26])[CH:18]=1)[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].B(Br)(Br)Br>ClCCl>[Cl:28][C:14]1[CH:13]=[C:4]([CH:3]=[C:2]([Cl:1])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:25]([CH3:26])[CH3:27])[CH:18]=1)[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 86584085HCID 86584085, compound

Product 1

HCID 86584086HCID 86584086, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from Step C (26 mg, 0.060 mmol) in dichloromethane (1 ml) at room temperature was added boron tribromide (1M in dichloromethane, 0.12 ml, 0.12 mmol). After the addition, a brown solution was obtained which was stirred at room temperature for about three hours. An additional 4 equivalents of boron tribromide was added and the mixture was stirred for 15 minutes at room temperature. A brown precipitation formed. The reaction was quenched with water (5 ml) and extracted with dichloromethane (3×10ml). The combined extracts were dried, filtered, and concentrated, and the residue was purified by preparative TLC (7% methanol in dichloromethane) to give the title compound (13 mg) as an off-white solid. MS (APCl−) Calc: 423.0, Found: 422.0 (M−1).

Workup

  1. additionAfter the addition
  2. customa brown solution was obtained which
  3. stirringthe mixture was stirred for 15 minutes at room temperature
  4. customA brown precipitation
  5. customformed
  6. customThe reaction was quenched with water (5 ml)
  7. extractionextracted with dichloromethane (3×10ml)
  8. customThe combined extracts were dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customthe residue was purified by preparative TLC (7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3fc40aacce2740eca5c69d5da9164d3d
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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