Tetrahydrofuran → HCID 21254081, compound

HRID 1292385Notes

Reaction equation

HRID 1292385 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BrH:36].[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([Br:36])=[C:12]2[CH2:18][CH2:19][N:20]1[C:21](=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1548084HCID 1548084, compoundHCID 21226041Pyridinium hydrobromide

Product 1

HCID 21254081HCID 21254081, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2-(5-benzyloxy-1H-indol-3-yl)ethyl]isoindole-1,3-dione (800 mg in a mixture of dry 25 mL tetrahydrofuran and 25 mL dry chloroform) at 0° C. was added pyridinium hydrobromide perbromide (666 mg) and the mixture stirred at 0° C. After 23 minutes the reaction was quenched by the addition of saturated sodium bicarbonate and extracted with ethyl acetate. The organic portion was washed with saturated sodium bicarbonate (3×) and 0.3M sodium bisulfate (3×) then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:2) followed by repurification by flash chromatography on silica gel (methylene chloride) gave the title compound (632 mg).

Workup

  1. customAfter 23 minutes the reaction was quenched by the addition of saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic portion was washed with saturated sodium bicarbonate (3×) and 0.3M sodium bisulfate (3×)
  4. dry with materialthen dried over magnesium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:2)
  7. customfollowed by repurification by flash chromatography on silica gel (methylene chloride)

Sources & evidence

ORD record
ord-1db84f42bc10456e9ee40c0682c20209
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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