Boron tribromide → HCID 59426403, compound

HRID 506093Notes

Reaction equation

HRID 506093 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]([CH2:25][CH3:26])[C:14]3[C:19]([C:20]=2[C:21]#[N:22])=[CH:18][CH:17]=[C:16]([O:23]C)[CH:15]=3)[CH:7]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:27])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]([CH2:25][CH3:26])[C:14]3[C:19]([C:20]=2[C:21]#[N:22])=[CH:18][CH:17]=[C:16]([OH:23])[CH:15]=3)[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59424974HCID 59424974, compound

Product 1

HCID 59426403HCID 59426403, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid ethyl ester (1.65 g, 4.37 mmol) in DCM (20 mL) is added 1M BBr3 in DCM (13.12 mL) over a period of 20 min. The reaction mixture is stirred further 1 h at room temperature and then the solvents are removed under reduced pressure. The residue is dissolved in MeOH and then poured into cold water. The precipitate is collected by filtration and washed with hexane and dried in vacuo to afford [3-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid ethyl ester (1.5 g, 98%).

Workup

  1. customthe solvents are removed under reduced pressure
  2. dissolutionThe residue is dissolved in MeOH
  3. additionpoured into cold water
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ebe51a2413c3471d811f9bc4aadb93f6
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

Loading…