Bromine → 3-Bromo-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1h-indole

HRID 423328Notes

Reaction equation

HRID 423328 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[Br:26]Br>CN(C=O)C>[Br:26][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([C:14]3[N:13]=[C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[CH:3]=4)[O:16][N:15]=3)[CH:18]=2)[NH:22][CH:21]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 593183535-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

Product 1

HCID 593183903-Bromo-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1h-indoleYield 29.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole (D5) (450 mg, 1.27 mmol) dissolved in DMF (12 ml) was added bromine (213 mg, 1.35 mmol) dropwise. Stirred for 15 minutes, evaporated off the DMF, added diethyl ether (70 ml) and washed with water (2×70 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from diethyl ether/hexane to give 160 mg of the title compound as a white solid. δH (400 MHz, d6-DMSO) 1.37 (6H, d), 4.88 (1H, sept), 7.44 (1H, d), 7.59 (1H, dd), 7.72 (1H, d), 7.91 (1H, dd), 8.13-8.32 (3H, m). MS (ES) C19H1579BrClN3O2 requires 431; found 432 (MH+).

Workup

  1. customevaporated off the DMF
  2. additionadded diethyl ether (70 ml)
  3. washwashed with water (2×70 ml)
  4. dry with materialDried over MgSO4
  5. customevaporated off the solvent
  6. customThe residue was crystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-ad0d359dc9a746e79d3b5f7bc58c05f0
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

Loading…