Boron tribromide → HCID 59426403, compound

HRID 252583Notes

Reaction equation

HRID 252583 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-dc80b74e56194bc3890cfa1711c5bdaa
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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