Bromine → HCID 22676785, compound

HRID 2292697Notes

Reaction equation

HRID 2292697 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:23]Br>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]2[Br:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 22676785HCID 22676785, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of ethyl 5-benzyloxyindole-2-carboxylate (21.9 g, 74.0 mmol) in DMF (30 mL) was added dropwise over 10 min a solution of bromine (11.83 g, 74.0 mmol, 3.8 mL) in DMF (40 mL). After stirring an additional 20 min at room temperature, the solution was partitioned between 3 N HCl and ethyl acetate. The organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate, water and saturated brine, then dried (MgSO4), filtered and concentrated to leave a white solid. The solid was recrystallized from ethyl acetate to provide the title compound (19.6 g, 71%). 1H NMR (400 MHz, CDCl3) δ 8.96 (br s, 1H), 7.52-7.30 (m, 6H), 7.15-7.10 (m, 2H), 5.14 (s, 2H), 4.46 (q, J=7.1 Hz, 2H), 1.46 (t, J=7.1 Hz, 3H).

Workup

  1. customthe solution was partitioned between 3 N HCl and ethyl acetate
  2. washThe organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate, water and saturated brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave a white solid
  7. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e341b49322f5453293acfed6ccdd4a85
Source dataset
uspto-grants-1997_11
Patent number
US05684032

Reaction notes

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