N-bromobutanimide → HCID 10623988, compound

HRID 1069591Notes

Reaction equation

HRID 1069591 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:28]N1C(=O)CCC1=O.C(O[C:44](=[O:55])CC1C2C(=CC=CC=2)NC=1)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:55][CH3:44])[CH:18]=2)[N:13]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:12]=1[Br:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 19603827Benzyl (1H-indol-3-yl)acetateHCID 86757071HCID 86757071, compound

Product 1

HCID 10623988HCID 10623988, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Bromo-5-methoxy-!-(phenylmethyl)-1H-indole-3-acetic acid benzyl ester. N-Bromosuccinimide (450 mg, 2.5 mmol) was added to 910 mg (2.5 mmol) of 5-methoxy-1-phenylmethyl)-1H-indole-3-acetic acid benzyl ester in 75 mL of carbon tetrachloride and the mixture stirred for 0.5 hour. After washing with Na2S2O3 solution, water and saturated NaCl solution and drying (Na2SO4), the CCl4 was removed at reduced pressure. The residue was chromatographed on silica (eluted with methylene chloride) and crystallized from ether/hexane to give 765 mg (67% yield) of 2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid benzyl ester, mp, 89-90° C.

Workup

  1. washAfter washing with Na2S2O3 solution, water and saturated NaCl solution
  2. dry with materialdrying (Na2SO4)
  3. customthe CCl4 was removed at reduced pressure
  4. customThe residue was chromatographed on silica (eluted with methylene chloride)
  5. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-9309cfefe0054255aeba783ee205d80d
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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