2-Bromopyridine → HCID 18374757, compound

HRID 555784Notes

Reaction equation

HRID 555784 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.CC([O-])(C)C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>O1CCOCC1>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 12682914-Amino-1-Boc-piperidineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 18374757HCID 18374757, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-Amino-1-Boc-piperidine (2.0 g, 9.7 mmol), 2-Bromo-pyridine (1.93 mL, 19.4 mmol), NaOtBu (2.7 g, 27.1 mmol), 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (472 mg, 1.16 mmol) and Tris(dibenzylideneacetone)dipalladium Chloroforme Complex (620 mg, 0.58 mmol) in dioxane (10 mL) is heated to 90° C. After completion, the reaction mixture is quenched by H2O, DCM is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a white powder; ES-MS: M+H=278.3: AtRet=4.75.

Workup

  1. customAfter completion, the reaction mixture is quenched by H2O, DCM
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e615b59e0a454714b5260c81ca5633dc
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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