3,4-Dibromopyridine → HCID 10111818, compound

HRID 1351514Notes

Reaction equation

HRID 1351514 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.[Br:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:25]=1Br>CC(O)C>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:25]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[Br:19])[CH2:4][CH2:5]1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 8171063,4-DibromopyridineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 10111818HCID 10111818, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of benzyl-4-(aminomethyl)piperidine-1-carboxylate (EXAMPLE 13, Step 1, 0.20 g, 0.81 mmol), 3,4-dibromo-pyridine (Chem. Abstracts, 58:5627) (0.19 g, 0.81 mmol) in IPA (0.5 mL) was heated at 100° C. in a sealed reaction tube for 7 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (DCM IPA hexane)) to give 4-[(3-Bromo-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester. M.S. (M+1): 405.27

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel chromatography (DCM IPA hexane))

Sources & evidence

ORD record
ord-178a1dc1d9294f59a6a6a7064c79b542
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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