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2-Bromoaniline → 5-(2-bromo-phenylcarbamoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 83981
Notes
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Reaction equation

HRID 83981 reaction equation
C[Al](C)C.[Br:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].C[O:14][C:15]([C:17]1[CH2:18][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][CH2:21][CH:22]=1)=O>ClCCl>[C:26]([O:25][C:23]([N:19]1[CH2:18][C:17]([C:15](=[O:14])[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[Br:5])=[CH:22][CH2:21][CH2:20]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 119922-BromoanilineHCID 111284441-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 689278695-(2-bromo-phenylcarbamoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

Trimethylaluminium (2M in heptane, 3 ml) was added dropwise to a solution of 2-bromoaniline (860 mg) in dichloromethane (15 ml). After gas evolution ceased, 5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (Chem. Commun. 1999, 1757-1758, 1.2 g) dissolved in dichloromethane (10 ml) was added and the resulting mixture was refluxed for 5 hrs. The solution was cooled to 0° C., quenched by careful addition of saturated aqueous sodium bicarbonate (10 ml) and extracted with dichloromethane. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 85:15) to afford 5-(2-bromo-phenylcarbamoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.2 g), which was characterised by its mass and NMR spectra.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was refluxed for 5 hrs
  3. customquenched by careful addition of saturated aqueous sodium bicarbonate (10 ml)
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 85:15)

Sources & evidence

ORD record
ord-ef6ef8d06845496a96b911312e08976f
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846907B2

Reaction notes

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