Ethyl Acetate → HCID 50991639, compound

HRID 240849Notes

Reaction equation

HRID 240849 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:19][CH:20]=3)[N:15]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:14]=2)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(Cl)Cl>[N:22]1([C:18]2[CH:17]=[C:16]3[C:21]([C:13]([C:10]4[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=4)=[CH:14][N:15]3[C:28]3[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=3)=[CH:20][CH:19]=2)[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 50991638HCID 50991638, compound

Product 1

HCID 50991639HCID 50991639, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (BBr3, 17 μL, 0.182 mmol) was added to a mixture solution of 3-(4-methoxyphenyl)-6-(piperazin-1-yl)-1-(pyridin-4-yl)-1H-indole (14 mg, 0.036 mmol) in methylene chloride (0.5 mL) at −78° C. After stirring at room temperature for 15 hours, the reaction solution was added to a mixture solution of saturated sodium bicarbonate aqueous solution and ethyl acetate and then extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The target compound (12 mg) was obtained as yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-1bee252900cd4fb2b5ce5e5b3ad31a61
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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