Water → HCID 66681649, compound

HRID 1964518Notes

Reaction equation

HRID 1964518 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O.O>O1CCCC1>[Br:23][C:12]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:9]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 66681296HCID 66681296, compound

Product 1

HCID 66681649HCID 66681649, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 6-[1-(t-butoxycarbonyl)-1H-pyrrol-2-yl]nicotinate (835 mg, 2.76 mmol) synthesized in Example (11a) was dissolved in tetrahydrofuran (30 mL), and cooled to 0° C. N-Bromosuccinimide (492 mg, 2.76 mmol) was added, and stirring was carried out at room temperature for 19 hours under nitrogen atmosphere. Water (30 mL) was added, and extraction was carried out with diethyl ether (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%) to afford the desired compound (712 mg, yield 68%) as a pale yellow oil.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%)

Sources & evidence

ORD record
ord-5be1f771f27a4a86951fe6c20d616b1d
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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