Boron tribromide → HCID 10541824, compound

HRID 1069586Notes

Reaction equation

HRID 1069586 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:20][C:21]([NH2:23])=[O:22])=[C:6]([CH3:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:20][C:21]([NH2:23])=[O:22])=[C:6]([CH3:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10566753HCID 10566753, compound

Product 1

HCID 10541824HCID 10541824, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.45 g (4.7 mmol) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide and 14.1 mL (14.1 mmol) of 1M BBr3 in methylene chloride was reacted as described in Example 2, Part C to give after chromatography on silica (eluted with EtOAc/hexane, then EtOAc) 908 mg (66% yield) of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 200-208° C.

Workup

  1. customto give after chromatography on silica (
  2. washeluted with EtOAc/hexane

Sources & evidence

ORD record
ord-01ab2fd66b61482ea05d00a6a9cabc1f
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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