Boron tribromide → HCID 10248281, compound

HRID 2181800Notes

Reaction equation

HRID 2181800 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:17]([C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22482377HCID 22482377, compound

Product 1

HCID 10248281HCID 10248281, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred and cooled solution of 6-ethyl-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (38 mg, 100 μmol) in dichloromethane (2 mL) was treated drop-wise under nitrogen at −30° C. with a solution of 1.0 M boron tribromide in dichloromethane (500 μL, 500 μmol). After the addition was completed, the reaction mixture was allowed to warm to room temperature and was stirred for four hours. The reaction mixture was cooled to −30° C. and quenched with methanol (600 μL). The solvent was removed in vacuo to yield the title compound (36.5 mg, 100 μmol, 100%), which was confirmed by LCMS (ES−, FA, CV=20 or 5);

Workup

  1. additionAfter the addition
  2. stirringwas stirred for four hours
  3. temperatureThe reaction mixture was cooled to −30° C.
  4. customquenched with methanol (600 μL)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8f7cafd69aa94718bf39696f1b9fbbb6
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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