N-bromobutanimide → HCID 70896150, compound

HRID 2403668Notes

Reaction equation

HRID 2403668 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Br:20]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:20][C:3]1[C:4]2=[N:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH:8]=[C:9]2[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 70896151HCID 70896151, compound

Product 1

HCID 70896150HCID 70896150, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of benzyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate (830 mg, 3.29 mmol) in N,N-dimethylformamide (19 mL) was added N-bromosuccinimide (609 mg, 3.42 mmol). The reaction was allowed to gradually warm to room temperature and stir over the weekend. The reaction was diluted with ethyl acetate and washed successively with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, water, and brine. The organics were dried over sodium sulfate, filtered, and concentrated to give the title compound (1.08 g, quantitative). +ESI (M+1+H) 333.0; 1H NMR (400 MHz, DMSO-d6, δ): 12.06 (br. s., 1 H), 8.99 (d, J=1.8 Hz, 1 H), 8.37 (d, J=2.0 Hz, 1 H), 8.14 (d, J=2.9 Hz, 1 H), 7.52 (m, 2 H), 7.41 (m, 3 H), 5.41 (s, 2 H).

Workup

  1. washwashed successively with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, water, and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-30d820e013824be4b5dca2bbf2bef63c
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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