Boron tribromide → HCID 59426403, compound

HRID 907191Notes

Reaction equation

HRID 907191 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 mmole) in DCM (20 mL) was added 1M BBr3 in DCM (13.12 mL) over a period of 20 min. The reaction mixture was stirred further 1 h at room temperature and then the solvents were removed under reduced pressure. The residue was dissolved in MeOH and then poured into cold water. The precipitate was 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 were removed under reduced pressure
  2. dissolutionThe residue was dissolved in MeOH
  3. additionpoured into cold water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-63d619cccdea4446bd33290ea2611f31
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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